Welcome to Dear Kara, a weekly column where I address your dating dilemmas, communication challenges and relationship quandaries with honesty, nuance and practical tools you can actually use.

All identifying details have been changed.

If you’d like to submit a question, click the button below. If I select your question, I will send you a personal email with the response (in other words, you don’t need to be a Substack subscriber to submit, so don’t be shy.)

Ask Kara Here

On to this week’s submission!

Dear Kara…

I’m 41 and I’ve never been in a long-term relationship. I’ve never lived with a partner and haven’t had a long-term sexual relationship. I’ve had a couple of flings and situationships, but I’m worried that if someone I date knows I haven’t had a long-term relationship, they’re going to think it’s a giant red flag.

I change the subject, make a joke and internally panic anytime someone asks me about my relationship history. What am I supposed to say? More importantly, if not having had a long-term relationship at 41 is a red flag, how am I ever going to have the long-term relationship I want?

— Feeling Unqualified

Dear Qualified,

I’m addressing you as Qualified because I suspect you are far more qualified to be in a long-term relationship than you may give yourself credit for.

First, a couple of interesting stats to put things in perspective. Did you know that in 2026, nearly half of adults under 30 are currently single, according to Pew Research Center, and among college graduates, only about one-third report having had a serious boyfriend or girlfriend through most of college?

So if your 20s didn’t include one long-term relationship after another, and your 30s were a time for prioritizing your career or getting more serious about dating, you’re not necessarily missing some universal relationship experience everyone else managed to collect.

People are entering relationships, building partnerships and reaching major milestones on very different timelines. Sometimes we imagine everyone is following a certain relationship timeline, and it just isn’t true. I can share this with full confidence after speaking with thousands of singles of all different ages who are looking for their first long-term relationship.

So, let’s start by challenging the definition of relationship history.

Redefining Relationship History

While I haven’t met with you personally, my guess is that you have long-standing relationships with your family, whether they are relationships you’d like to replicate or not.

You have relationships, and maybe even breakups, with friends.

You’ve likely had roommates, coworkers and people you’ve dated, even if those relationships never turned into a committed partnership.

More importantly, you’ve had a wide range of experiences that have allowed you to trust, feel disappointed, be in conflict, set boundaries, offer forgiveness, practice communication, feel attraction, experience rejection, show loyalty, feel frustration and experience intimacy. The list goes on.

Whether you realize it or not, these experiences have taught you something about how you operate in relationship with another human being.

That is relationship history.

When I work with clients on the Relationship History chapter of their Love Manual, I’m not particularly interested in creating a timeline of their long-term exes.

Instead, I want to understand patterns within their human relationships.

So, I’ll ask questions like:

1. What dynamics have made you feel seen and understood in your relationships with other people?

2. Where have you consistently found yourself frustrated or running into challenges?

3. How do you typically handle conflict? And what happens when the other person handles conflict differently?

4. What types of people bring out the best in you?

5. What types of people bring out a version of yourself that you don’t particularly like?

6. When have you felt appreciated by another person? What was that person doing specifically that made you feel that way?

7. What role do you naturally take in relationships? Caretaker, problem-solver, peacekeeper, planner, pursuer, the independent one?

8. What have you learned about your boundaries from relationships that didn’t work?

9. What do you need from another person in order to feel safe enough to be vulnerable?

10. Looking at all of your relationships, what patterns do you want to repeat in a long-term partnership? What patterns do you want to leave behind?

These questions don’t require you to have a ten-year marriage, a string of serious exes or a history of living with a partner.

The point of exploring your Relationship History chapter is to help you understand yourself in relationships so that you can communicate to future potential partners what works for you and what you are seeking in a long-term relationship.

Experience Isn’t the Same as Self-Awareness

Yes, it’s true that there are some things you simply won’t know until you experience them.

You won’t know what it’s like to share a home with a committed partner until you share a home with a committed partner.

Each sexual relationship is going to be different than the last.

You can’t predict (and know how to handle) every little thing that will challenge you in a committed partnership.

Another truth?

A new relationship is new to the other person who is in it, too.

I have worked with clients who have been married, sometimes more than once, and are still discovering their boundaries and how to communicate their needs.

I have worked with clients who have lived with a partner for five years and are trying to figure out their own conflict patterns.

Others have had a robust sexual history and are still figuring out what makes them feel safe, desired and connected in a long-term relationship.

Experience doesn’t always equal self-awareness.

Your question tells me you are curious enough to want to explore why your perceived lack of long-term relationship history has become a block for you.

That’s self-awareness at its best, my friend.

So, just because you’ve never had a long-term relationship certainly doesn’t mean you’re not prepared to enter into one successfully. And each new relationship presents a new dynamic for both people to explore.

The Other Side of the Story

Now let’s consider how your lack of “traditional” relationship experience could actually work for you.

Maybe you’re more eager, excited and willing to put in the effort it takes to build a partnership for the first time.

Perhaps you haven’t accumulated years of unhealthy relationship patterns that you’re trying to unlearn. (Side note: Kudos to those who are doing this work!)

Maybe you’re approaching partnership with a tremendous amount of curiosity and openness around what a relationship can look like.

Consider this mindset shift:

Instead of walking into your next date thinking:

“Please don’t let them ask me about my relationship history, please don’t let them ask me about my relationship history…”

Walk in thinking:

“I’m excited to discover who this person is and what we could create together.”

Two very different energies.

One comes from the fear that someone will judge you for your perceived lack of relationship history. The other comes from confidence in your desire to have a long-term relationship with a compatible partner. Period.

Ok, so we’ve reframed the underlying “Am I a walking red flag?” fear.

Now let’s get to the other part of your question.

What do you say on a date when faced with the “Tell me about your relationship history…” prompt?

Read more

What’s meant to be will be.

If it’s going to happen, it’ll happen.

When I least expect it, they’ll find me.

I’m going to let the universe do its thing.

I understand the appeal of these statements when dating frustration is at an all-time high and my clients are ready to throw their hands in the air.

Dating, apps and first dates can be exhausting. Putting yourself out there only to be disappointed, ghosted, rejected or met with yet another person who isn’t quite right can make even the most optimistic dater wonder:

How much effort am I supposed to put into this?

Eventually, surrendering to the exhaustion can feel like relief.

Fine. Whatever happens, happens.

Lately, I’ve been noticing something in my coaching sessions that makes me want to look a little more closely at that sentiment.

Because “What’s meant for me won’t pass me by” can also come from a very helpful, deep place of knowing.

And it’s up to me to help my clients uncover what’s underneath each “What will be, will be.”

What’s Underneath the Belief?

I’ve found that two people can say, “What will be, will be,” but have two very different motivations behind it. Those motivations affect how they show up to dating and, subsequently, the likelihood of finding the relationship they desire. Which is why this matters in a coaching session.

One person might be thinking:

What will be, will be. I know I want a loving partnership. I don’t know when it will happen or exactly how I’ll meet this person, but I trust that they’re around the corner and I’m worthy of the relationship I want. I’m going to keep living, keep meeting people, keep putting myself in situations where connection can happen and let the rest unfold.

Another person might be thinking:

What will be, will be. I can’t take another disappointment. I’m tired of dating. I don’t want to get my hopes up again. I’m going to tell myself that if it’s meant to happen, it will and then I don’t have to put myself through this anymore.

Same starting sentiment, yet with very different underlying motivations.

“If it happens, it happens” can bring genuine peace. It can also be a protective layer over disappointment.

“I’ll meet someone when I least expect it” can reflect a beautiful trust in the unpredictability of life. It can also become a convenient reason to stop participating.

You don’t have to believe in fate, timing, the universe or divine intervention, but you do need to ask yourself:

Am I still actively moving toward the relationship I want?

For those of you experiencing the I can’t put myself through this anymore type of whatever will be, will be, take the break you need.

But recognize that when frustrated energy is driving the what will be, you probably won’t be moving through life with your chin up and your eyes open to possibility.

Take good care of yourself. Figure out how to once again open yourself up to all the directions your path to your person might take. If you need help with this, I am available to chat.

And trust that you can still be on the right road in the meantime.

10+ Years of Evidence

I’ve spent the better part of the last decade working with people around love and relationships.

I’ve been a professional matchmaker. I’m a dating and relationship coach. I’ve sat across from thousands of people who wanted the same basic thing: to find someone they could love and build a life with.

And I’ve heard thousands of love stories.

I can tell you this with a lot of confidence:

Very few of those stories happened the way the person thought they would.

For example:

The woman who thought she would be married to a man, have kids and a white picket fence in her mid-twenties instead discovered she was gay at 21 and her whole world opened up. Three or four serious relationships and the passage of Marriage Equality later, she met her person in her 40s and had the wedding of her dreams.

Oh, wait. That’s me.

The man who insisted on dating in his own neighborhood ended up with an old college acquaintance he reconnected with at a reunion. They lived in two different states, did long distance for several years, only to finally consolidate their lives and jobs in one spot. Last I heard, they were taking their parents on a cruise together.

The woman who went through a very contentious divorce with someone she thought was the love of her life came out the other side, started the business of her dreams, fell in love with herself and found her person in her early 60s.

The woman who wanted to get married in her late 20s and have two children by age 34 met the love of her life at 39, who happened to be a young widow with an infant and a toddler.

These are just a few examples of people who eventually found their person in a way that didn’t resemble the stories they had written for themselves.

They couldn’t have predicted where.

They couldn’t have predicted who.

They couldn’t have predicted the circumstances.

They couldn’t have predicted the events, experiences, relationships, moves or self awareness that would ultimately lead them to each other.

An Exercise for Those Trying to Get Back to Hopeful

Feel free to do your own data collection.

Think about the couples you know who have the relationships you admire most.

Maybe your parents or grandparents.

Your sibling and in-law.

Your best friend.

The friend who just got married.

The couple at work who have been together for 30 years.

The people whose relationships you look at and think, That’s what I want.

Then ask them:

Did it happen the way you thought it would?

When did you meet?

Where did you meet?

What were you doing with your life at the time?

Did you expect to meet someone then?

Did you think you would marry someone like this?

Did you know the relationship would become what it became?

Could you have predicted the path from your first meeting to the life you have now?

Ask people from different generations.

Different backgrounds.

Different walks of life.

I think you’ll find that the people who followed their own prescribed timeline are few and far between.

And some of the most extraordinary love stories?

The people living them could not have called the details if you’d given them a crystal ball.

One final interesting question to ask those who are coupled as you collect some data:

What would you have told yourself about dating prior to meeting your person?

Then take those words in and filter them through your new perspective on what will be, will absolutely be.

Maintain the Vision, Release the Script

This doesn’t mean you shouldn’t have a vision for your life. In fact, you know I strongly believe in creating your Vision of Partnership.

Maybe you want marriage. Maybe you want children. Maybe you want a partner to travel with. Maybe you want someone who knows that the best way to make a bad day better is tacos for dinner and zero follow-up questions until you’re ready to talk.

Understanding what you’re moving toward is a valuable exercise.

But there is a difference between having a vision and writing the entire script word for word.

The vision might be that you want a loving partnership, a life built with someone you adore.

The script is deciding exactly when, where and how all of it has to happen. Or believing it should come naturally or it should be as easy, or as difficult, as getting your master’s degree was.

When life doesn’t follow the script, it’s easy to believe something has gone wrong.

I get it.

And for some of us, releasing the script comes with grief. There are real timelines and circumstances that can’t be ignored. You don’t have to pretend that changing the vision of your future doesn’t hurt.

But grieving the way you thought it would happen doesn’t mean giving up on the possibility that something else still can.

You can maintain the vision while releasing the script.

You can want the relationship and still not know who you’re going to meet. Or when.

You can want a family and still not know what the path to that family will look like.

You can take a break from dating while still believing it’s worth it to try again when you are ready.

In the meantime:

You won’t know which invitation is going to matter.

Which move will change everything.

Which first “meh” date could open up your world in a way you never could have written or imagined.

Keep moving toward the Vision of Partnership you want, even if you have absolutely no idea how you’re going to get there.

I’m 95% certain it won’t happen the way you thought it would.

And based on thousands of love stories, I’m equally certain that doesn’t mean it won’t happen at all.

Because one day, you may look back at the life you’re living and realize the story was better than the one you wrote for yourself.

On a Personal Note…

Speaking of a better story than I could have written for myself, Jen and I have found ourselves in the Semi-Finals of America’s Favorite Couple contest.

Our friends and family have been voting for us for 7+ weeks - yeesh! If you’d like to get in on the fun, we’d love your vote. You can vote here. It’s free to vote once a day and if you cast any additional votes, the money goes to two very worthy causes, the LA Food Bank and Oceana. The contest runs through September 10th. Eeeee!

How did we end up in this position (other than the serious dedication of our loved ones)?

Fun fact about me: Jeff Goldblum is my man crush (random, I know - can’t resist the quirky, oddball type).

Several years ago, Jen got us tickets to his jazz piano show (yes, in addition to acting, he plays jazz piano). Prior to the show, Jeff was wandering around in the audience, chatting and taking pictures with everyone.

As he got close to us, Jen got her phone ready and I FROZE. I totally blew it. This is how close he was - that is my water bottle:

Fast forward to 7+ weeks ago. I see that the first prize in this contest is to meet Jeff Goldblum (and his wife), so I started to fill out the application, because obviously I need a REDO.

At some point, I noticed it was a voting thing and stopped filling out the profile. The next thing I knew, I received an email saying, “Welcome to the contest! Your profile is live!” I sent the link to Jen as a joke. While I was in a coaching session, she sent it to our friend group and we’ve been in 1st place ever since.

Except now.

As of last night, we made it into the SEMI-FINALS and the competition has increased tenfold!

So we are spreading the word, because I can’t leave this one up to What will be, will be. Operation Jeff Goldblum REDO is in full swing!

Welcome to Dear Kara, a weekly column where I address your dating dilemmas, communication challenges and relationship quandaries with honesty, nuance and practical tools you can actually use.

All identifying details have been changed.

If you’d like to submit a question, click the button below. If I select your question, I will send you a personal email with the response (in other words, you don’t need to be a Substack subscriber to submit, so don’t be shy.)

Ask Kara Here

On to this week’s submission!

Dear Kara…

Every time this time of year rolls around, I start to feel it.

The cicadas get louder. Football season starts. There’s even that slight shift in the air when you realize summer isn’t going to last forever.

And somehow, all of it brings me back to the fact that I’m single.

I know fall is around the corner, which means cuffing season is, too. Cuffing season feels like it has become almost as commercially unavoidable as Valentine’s Day. Suddenly, I’m supposed to be finding someone to settle in with before the first leaf hits the ground.

So I guess I’m wondering: Is fall actually the best time to start dating? Is cuffing season really a thing? Or have we all just collectively decided that colder weather = time to lock it down with someone?

-Preparing for Open Dating Season

Dear Preparing,

I feel you.

As a former teacher, this time of year brings up all kinds of emotions. The excitement of a new school year coupled with the nerves of meeting 25 new little faces and their families. And then I remember, that was years ago!

And now I have the good fortune of working one-on-one with people looking for love.

During cuffing season.

There’s no denying it.

For those who don’t know, it’s the unofficial dating season that typically starts around Labor Day and stretches through the colder months. It’s the time of year when single people supposedly become more interested in finding someone to “cuff,” or settle in with, as the temperatures drop.

Personally, I’ve always thought the term cuffing season felt a little bit like “you’ve been caught doing something wrong” season or respectfully, something more suited to the kink community. If we had to call it something, I’d opt for something lighter, like “snuggle in season.”

The idea is human: When the days get shorter and the weather gets colder, we naturally start craving companionship, coziness and someone to curl up with.

But before we get too hung up on the season ahead, I’d love to let you in on a little secret. The winter, spring and summer have their own versions of cuffing season.

After nearly a decade in matchmaking and date coaching, I’ve seen enough seasons of love to know this for certain.

And yet, everyone wants to know:

When is the best time to date?

My answer has always been the same:

Every season has its advantages. And every season has its challenges.

Most of the time when I am speaking with those who are frustrated with dating, the challenges come up first.

Winter

This argument makes sense because it’s true. People are traveling, shopping, wrapping presents, attending parties, managing family get-togethers and trying to hit end-of-year deadlines at work.

Calendars can be packed, so it’s easy to think, Why would I add dating to this?

But then there’s the other side of the winter coin.

People are thinking about family and the people who are most important to them. They’re going to holiday parties, attending gatherings and making New Year’s plans.

Maybe more than at any other time of year, they are thinking about who they want beside them.

And don’t get me started on winter’s fantastic date opportunities.

Cozy restaurants with fireplaces.

Movie nights in.

Cooking dinner together.

Wandering through holiday markets bundled up and with a warm beverage.

No wonder winter is often included in fall’s cuffing season.

It’s true that everyone might be busier, but connection is at the top of everyone’s mind, making it a very viable time to connect with someone special.

Spring

Spring has its own version of the maybe I should wait argument.

Side note: You see where I am going with this, yes?

After a long winter, some people feel like they need a minute.

Maybe you get the urge to start working out again. Or you want to refresh your wardrobe and get your house organized. Perhaps figure out what happened to your social life while you were wrapped up in a cozy blanket from November through March.

You may not feel like the most confident version of yourself, but spring has a cuffing season vibe of its own.

Everything feels new again.

The days get longer. The weather gets warmer. People start emerging from their homes. There’s an undeniable sense of possibility in the air.

Spring feels like a fresh start.

It’s a great time to get outside, start walking again, exploring your city, trying new things and meeting all the others who ready to shake off the winter.

There’s something wonderfully optimistic about dating in the spring. The fresh opportunity for love is in bloom.

Summer

Summer might be the easiest season to abandon dating.

Everyone has plans. People are at the lake or the cape or on two-week long vacations. People are trying to squeeze every possible ounce of fun and relaxation out of the few precious months of good weather.

So maybe it makes sense to wait for things to slow down.

Except...

Summer also gives you endless opportunities to actually go out and enjoy your life with someone who you might enjoy year round.

Patios, rooftop bars, baseball games, concerts, festivals, beaches, boats, picnics and long walks, oh my.

There are so many ways to create experiences together as opposed to sitting across from each other at a restaurant asking, “So, what do you do?”

And who doesn’t feel like the best version of themselves when they are having fun in the sun and feeling rested?

Fall

And here we are. The start of the official cuffing season. Fall.

The time when we are once again supposed to get serious about life.

School starts and work picks up. Activities ramp up, leagues start and calendars become structured and routine again. If you’re a parent, you likely add approximately 48 additional things to your growing list.

So who has time to schedule in dating?

Well...

The cuffing season concept didn’t appear out of nowhere.

Fall is the season of pumpkin patches, apple picking, football games, hayrides, Halloween parties, crisp walks, piles of leaves and sweaters and jackets.

Sweaters + Jackets = Fall Fun

You feel the pull toward a big comfy sweater and want to get cozy with someone who is on the same page.

My hope is that by now, you’re noticing the problem with trying to determine the perfect season to date.

Every season gives you a reason to wait.

And every season gives you a reason to start or keep going.

So instead of asking, “Is fall really the best time to date?” or “Is cuffing season really a thing?” there is a more important question I’d like you to consider.

The Question Behind the Question

Try asking yourself:

“Why does it matter to me whether this is the right season?”

The answer might tell you something important about what’s really keeping you from dating.

Read more

You think it.

You feel it.

You’re into the banter. You’re laughing. You’re genuinely interested in what they’re saying and you’re having a better time than you expected.

And then…

You keep your thoughts safely inside your head.

Whomp. Whomp.

The two of you go your separate ways, both likely thinking, “Well, I know I had a good time.”

Sometimes this scenario ends well. Someone bravely asks the other out again and a second date happens.

Often, though, daters walk away thinking, “Maybe I was the only one who was into that. Maybe they’re just a good dater. Did I just dream that connection? I’ll let them make the next move - just to see.”

Imagine if both people followed that logic.

The potential for missed connection when we're all performing the version of ourselves we think will be accepted is almost cringeworthy.

Based on my unique peek behind the curtain of modern dating, I can confidently say we’ve lost the art of simply telling another human being what’s actually happening inside of us.

We’re living in a moment when everyone is talking about vulnerability and authenticity. We want to show up as our “true selves.” We want deeper connections and meaningful relationships. We want emotional intelligence and availability.

And yet, when we’re sitting across from someone we’re attracted to, we suddenly become very good at editing our “true selves.”

Don’t say too much.

Play it cool.

Make them work for it.

Appear mysterious.

Don’t come on too strong.

It’s only the first date.

What if they don’t feel the same way?

What if I make things awkward?

All valid thoughts. Dating requires vulnerability and vulnerability can feel risky.

But sometimes, in our effort to protect ourselves, we make dating and connecting more difficult than it needs to be.

Hear me out. I’m not suggesting you turn your dates into therapy sessions in which you share every thought in an unfiltered stream of consciousness.

But I am suggesting you start to notice and name the things you are experiencing on dates that are meaningful, relevant, kind, curious or true.

“I’m Nervous.”

One of the most common things I hear from clients is some version of:

“I get so nervous on dates. I sit down and suddenly I’m talking a mile a minute. Or I can’t think of anything to say. I get flustered. I’m so excited to meet someone new and I want them to know all these things about me because I want to make a good impression. And sometimes I just stumble all over myself because I’m nervous.”

My response is usually very simple:

Tell them that.

Imagine sitting down at the bar and saying:

“Okay, full disclosure. I am nervous. First dates are so awkward for me, AND at the same time I’m really excited to be here. So if I ramble on a little bit, you’ll know exactly what’s happening.”

That’s it.

You haven’t made yourself less attractive.

In fact, you’ve probably endeared yourself to the person next to you at the bar.

You haven’t ruined the date.

You’ve likely made space to actually connect.

You haven’t overshared.

I would bet money you made the other person feel more comfortable being their authentic self.

And most importantly, you’ve simply given the other person context and a lovely, authentic glimpse of the real you.

Instead of wondering, Why is this person talking so much? Are they trying too hard? Do they even like me? your date knows:

Oh. They’re nervous because they care about this.

If you’re on the other end of the spectrum and you get quiet or standoffish when you’re nervous, instead of working so hard to be something you’re not, you could simply say:

“Just so you know, I can be quiet until I warm up. I’m actually really excited to meet you.”

You no longer have to spend half the date trying to hide the fact that you’re nervous.

And very often, once you put words to what’s happening inside you, you feel a tremendous sense of relief.

Your shoulders drop. You can breathe a little easier, laugh and settle in.

You can actually start not only being yourself, but truly enjoying yourself.

“I’m Really Enjoying This.”

Other clients have shared:

“I really liked this person. We talked nonstop. We had such a good connection. I felt like I had known them much longer than an hour and a half. It was so easy. But what am I supposed to say? I don’t want to be too much too soon.”

My answer is the same:

Tell them exactly what you just told me.

There is absolutely nothing wrong with looking across the table and saying:

“I’m really glad I am on this date with you.”

Or:

“I feel like our conversation flows so naturally. I can’t believe this is our first date.”

Or:

“It feels really good to have this kind of banter with someone.”

Or even:

“I was looking forward to tonight, but I didn’t expect to enjoy it this much.”

You don’t need to follow it with a five-minute explanation. Those little windows into your experience are powerful on their own.

How It Feels to Be on the Receiving End

When Jen and I were dating, there was a period when we were in that strange, ambiguous space where we were spending time? Seeing each other? Making dinner together? Talking about future plans? But hadn’t quite figured out what we were calling it.

We’d been on what felt like our twentieth version of a date.

One night, I was leaving her house. We were standing outside next to my car and Jen seemed… frustrated.

Or maybe unsettled.

I couldn’t really tell what this unfamiliar energy meant and out of confusion, I was probably rambling on about our twenty-first date.

Until what was in Jen’s head came out of her mouth.

She simply said:

“I’m tired of not telling you I love you.”

That’s it.

No carefully constructed conversation.

No drawn-out explanation of her feelings.

Not even the conventional string of those three game-changing words.

Just the truth of what was happening inside her in that moment.

And I said:

“Well, so am I.”

And that was how we first said “I love you” to each other.

It remains one of my favorite moments in our relationship because of how incredibly human it was.

She had no idea how I would respond or if I felt the same way. She just knew she was tired of keeping something important inside herself.

So she granted me access to her experience.

And in doing so, she gave me the opportunity to comfortably share mine.

I often think about that moment when my clients are hesitant to share their experiences.

The Kindness of Reducing Uncertainty

The uncertainty in dating is undoubtedly one of the hardest parts of the search for your person.

You go home from a date and wonder:

Did they like me?

Were they attracted to me?

Did they think we had chemistry?

Why haven’t they texted?

Will I add them to the “Ghosted” list?

We’re living in a world where speedy certainty is all but guaranteed.

Amazon tells us how many stops away our package is.

Siri gives us a response in seconds.

Chatti, as I affectionately call ChatGPT, will happily answer our questions and then ask a follow-up to guide us toward additional clarification.

And then we go on a date and must sit with an enormous amount of face-to-face human uncertainty.

So, one of the kindest things you can do on a date is to let them in on your experience.

It’s as simple as…

“I’m so happy we did this. I’d love to do it again.”

Or:

“I had more fun than I expected!”

Or:

“Honestly, this was a great way to spend a Wednesday night.”

Or, if it’s clear that the connection isn’t there:

“This isn’t easy to say. I’m not really feeling the romantic connection I’m looking for. But what is easy to say is that you are wonderful. 10 out of 10, would recommend you to one of my friends.”

Or:

“I really appreciate you taking the chance on this date. I don’t think we’re a match, but I’m so happy to know good people like you exist in this crazy dating landscape. Your future person is very lucky.”

Let Them Into Your Experience

The goal of dating isn’t to present the most polished version of yourself, say everything “perfectly” or avoid awkwardness at all costs.

The goal is to allow another human being to experience you.

Sometimes that means letting the meaningful or clarifying thought that’s been living rent free in your head become part of the conversation.

It doesn’t guarantee they’ll feel the same way.

It doesn’t guarantee a second date.

And it definitely doesn’t guarantee you’ll avoid every awkward moment.

But it does mean the person sitting across from you has the chance to know you a little better.

And maybe that’s the point.

If we all want vulnerability and authenticity, we have to be willing to offer it, too.

Welcome to Dear Kara, a weekly column where I address your dating dilemmas, communication challenges and relationship quandaries with honesty, nuance and practical tools you can actually use.

All identifying details have been changed.

If you’d like to submit a question, click the button below. If I select your question, I will send you a personal email with the response (in other words, you don’t need to be a Substack subscriber to submit, so don’t be shy.)

Ask Kara Here

On to this week’s submission!

Dear Kara…

I keep seeing “emotionally available” listed as a must-have on dating apps. I know it’s supposed to be a good thing, but what does emotional availability actually mean?

How do I know if someone has it? How do I know if I’m emotionally available?

- Emotionally Confused

Dear Confused,

I’m so glad you asked. The desire for emotional availability comes up all the time in my sessions. And increasingly so over the last couple of years.

And while this might be a hot take, it’s based on thousands of conversations about relationships over the last decade.

Let me explain.

What Emotional Availability Means to You

When I used to meet with potential matchmaking clients and they shared their wishlists, emotional availability was usually somewhere near the top. But what it meant for each person was often determined by what was lacking in former relationships or dating experiences. Here’s what it sounded like once I did a little digging.

“She just didn’t understand me.”

“He wasn’t supportive.”

“I didn’t feel seen or heard.”

“They couldn’t express their feelings.”

So then I would ask,

“What didn’t she understand?”

“What makes you feel supported?”

“What could someone do to make you feel seen and heard?”

“How do you know when someone is expressing their feelings?”

Most could articulate the answers to these questions without pause. Which gave us a really wonderful starting point for what emotional availability looked like and felt like for them. And what they wanted, more specifically, in a relationship going forward.

I’ve found that emotional availability in a relationship has two parts. Not only does the person you’re dating need to be willing to show up emotionally, but you need to be able to communicate what emotional availability actually means to you.

Emotional availability can look very different from person to person.

For some, emotional availability might mean that when they’ve had a terrible day, their partner is willing to listen without immediately trying to solve the problem.

For others, it might mean having a partner who will collaborate with them on finding a solution.

It could mean being able to say, “I’m really upset right now, but I need a little time to figure out what I’m feeling before we talk about it.”

It might mean being able to identify what you’re feeling, regulate your emotions and explain why you’re upset without blaming the other person.

It might mean being able to have a hard conversation without shutting down, disappearing or turning the entire conversation into a defense of yourself.

Or it might mean something as simple as: “If I’ve had a hard day, I want to be able to tell you about it, put it behind me and go out for tacos.”

There isn’t one brand of emotional availability.

Emotional Availability Starts With Figuring Out What You Need

This is where I think we sometimes make dating unnecessarily complicated.

We use words like “emotionally available,” “emotionally intelligent” and “good communicator” as though everyone has the same definition.

Or we think that we are somehow behind, in the dark or lacking if we’re not clear on what exactly those terms mean.

None of which is true.

Figuring out emotional availability means getting curious about what works for you.

For example:

Do you need someone who asks how your day was?

Do you want someone who knows when you need a hug instead of advice?

Do you want someone who can sit with you when you’re sad without trying to make the sadness go away?

Do you want someone who can tell you when they’re struggling rather than expecting you to figure it out?

Do you need someone who can make space for your difficult day when they’ve had a difficult day too?

Do you need someone who has the ability to tell you they are depleted and need some time to themselves?

We may not have the capacity to give each other everything in every moment, but we can communicate that. And that counts as emotional availability, too.

Look for the Response, Not the Perfect Reaction

So how do I know if someone just isn’t capable or willing to be emotionally available?

You’ll feel it.

I often think of a No Vacancy sign.

It’s late at night. You’re on a road trip and your car breaks down. You know there’s no way someone will be able to service it until the morning. You can see the No Vacancy sign blinking in the distance.

When you arrive on foot, the front desk attendant says, “Sorry, no vacancy.”

You turn around and leave, feeling scared and on your own to deal with the situation.

But imagine...

You go back in and explain, “Hey, my car broke down about a half mile back. I know there isn’t anything I can do until tomorrow morning. Would you mind if I hang out here so I don’t have to sleep in my car?”

Now you’ve communicated what you need.

If the attendant says, “Again I apologize, but you’re on your own and you can’t stay here,” this is what being with someone who is emotionally unavailable can feel like.

You’ve made a reasonable request. They’ve heard it. And they’ve made it clear there is no room for you.

But what if the attendant says, “Sure.”

There’s some room for further communication.

And what if the attendant says, “Ugh, I’m so sorry. Let me see what I can do. We may have some blankets and a pillow to make you as comfortable as possible while you wait. Do you need to charge your phone?”

You instantly feel taken care of.

Full speed ahead. Well, in a relationship, that is.

For the record, though, I would not expect someone you’ve just started dating to automatically show up with the blankets, pillow and phone charger.

In early dating, the “Sure” may be the most meaningful response.

You’re still learning each other. You may not know what makes the other person feel cared for yet. You may not know whether they want a hug, advice, space or tacos for dinner. Yet.

Some people just get it. They seem to instinctively know how to make you feel safe and cared for.

Some people need specific instructions to your heart.

That doesn’t necessarily make them emotionally unavailable. It simply means they need you to communicate what works for you.

The easiest way to determine emotional availability is to

Read more

Dear Kara…

Dear All,

Dear Kara… and my regular Friday posts will be back next week.

This week, I’m adding to the Lifestyle, Habits and Traditions chapter of my own Love Manual as Jen and I celebrate our birthday month tradition of visiting a place we’ve never been to.

This year it’s Banff or bust!

To hold you over, I’ve compiled a list of my Top 5 Most Read Posts (it’s been fun to see what is resonating most). Enjoy!

5.

4.

3.

2.

1. (It’s a tie!)

Until next week, signing off and getting into relaxation mode and nature. Can’t wait to fall in love with a new place.

xo,

K

For these clients, coaching sessions are a perk that comes along with their matchmaking package. It’s a chance for us to get to know one another, understand what someone is looking for and build a solid foundation before they sit across from their next first date.

Most clients bravely show up to our first session not knowing what to expect.

I will often hear…

“Honestly, I’ve never done this before and I’m not sure what we’re going to talk about.”

Sometimes I get the sense clients think they are in for a crash course on great first date ideas or how to send a text message that leads to a second date.

And sometimes we will talk about those things. After nearly a decade as a professional matchmaker and dating coach, I’ve certainly accumulated plenty of practical advice. I’ve seen enough first dates, second dates, ghosting, miscommunication, awkward texting and relationship beginnings and endings to easily go for ten rounds of tactile advice.

But that’s rarely what coaching ends up being about.

I Was Once the Client

Each time I greet a new face, I try to remember that I have been in their shoes.

I was once the client.

Ironically, or maybe not so ironically, as I do believe the universe always has our backs, a chance meeting with a career coach is what led me to matchmaking in the first place.

And my session was a perk, too.

I was working for a startup that offered all kinds of creative compensation. This perk just happened to be worth its weight in gold.

It literally changed the trajectory of my life.

My coach’s name was, and still is, Becky Berry. She asked about my career path up until that point, just like I ask my clients about their relationship history and what dating looks like currently for them.

Before I knew it, I had revealed that I had been a fourth-grade teacher for 10 years, left education for a career in fashion, won a reality competition show and had done some writing as well as public speaking.

But I didn’t stop there.

I also shared how important my personal relationships were to me, how coming out in my early 20s changed the course of my life and how much I cared about my LGBTQ community.

I went on to say that I had been connecting people with new friends, jobs, apartments and romantic opportunities for as long as I could remember.

I’m not sure what I was expecting from Becky Berry, but once I came up for air, I swear I heard the chirping of crickets.

Now I know she was just leaving room for everything I had just shared to land.

What she did next was brilliant.

She suggested I think about the common threads in what I had shared and then type those words into LinkedIn to see what kinds of positions popped up.

That was the action item that led me to matchmaking.

I followed through on the plan and typed in “Love, Connection, LGBTQ…” and the position for “LGBTQ Matchmaker” was at the top of the search results.

Three interviews and now almost a decade later, matchmaking has turned into coaching people of all identities into the relationships they want. I’ve never felt more aligned with my work than I do right at this very moment.

I share this story because my coaching session with Becky could have looked completely different if she had been sitting across from someone else.

No two coaching sessions take the same direction.

So sometimes it’s easier to explain to a new client what coaching isn’t.

Coaching Isn’t Like Hiring a Personal Trainer

If you hire a trainer because you want to run a marathon, the finish line is usually pretty clear.

The trainer assesses where you’re starting, creates a workout and nutrition plan, you follow the plan, run your marathon and cross the finish line.

The kind of coaching I do is different.

My sessions often start with:

• Frustration with the apps

• Confusion about why effort is not paying off

• A string of disappointing relationships

• A big gap in time since someone last dated

• Dozens of first dates that haven’t led to seconds

• A pattern of attracting the same type of incompatible partner

• A scarcity mindset

• A certain block around dating

Before we build a plan, we need to explore where my client has been, where they currently are and what they want next.

We take all of that information and begin to document and organize it in their Love Manual. We use it to figure out where they want to go and plot a course for how to get there.

This process looks different for everyone.

Coaching Isn’t Therapy Either

However...

Therapy + Coaching = A Powerful Combo

Therapy helps us understand our past, heal old wounds, process grief, make sense of painful experiences and understand why we do what we do.

Coaching picks up the torch, armed with all that understanding of yourself, and helps you let the work you’ve done work for you.

Now that you know yourself better, you get to decide:

• What you want to do with that information

• How you’d like to communicate your needs

• How and when you establish boundaries

• Whether or not you choose to do things differently

• What a relationship that reflects the person you’ve become looks like

Coaching is about reflecting, getting curious, strategizing, gaining perspective, making informed decisions and following through on your plans.

Becky Berry had no idea what my finish line was, but she asked the questions and allowed me to find the answers that would get me there.

Which leads me to my two favorite questions to ask new clients:

What kind of relationship do you look forward to with your future partner?

What’s really getting in your way of finding the relationship you want?

The answers are different for everyone.

But here’s what I’ve found to be the same for most of my clients, and the reason coaching sessions tend to be such a productive surprise for those who were skeptical to begin with:

Some common examples of what clients see as getting in the way of finding the relationship they want include:

• A shrinking dating pool

• Circumstances that always seems to come before dating

• A life that’s too busy for dating

• Ambivalence around even wanting a relationship

• A tendency to lose themselves in a relationship or attract the wrong people

Coaching is the work of discovering what’s underneath the problems you can see and devising a strategy to change the game.

“There Just Aren’t Enough People to Date.”

When this is the barrier a client sees, we have to acknowledge that sometimes it’s a reality.

If you work from home, your closest friends are married and your social life has slowed down over the years, meeting someone new isn’t easy.

But coaching isn’t simply stopping at the fact that your dating pool is currently limited.

It’s about finding out what you have control over and how you can shift your thoughts and actions in a way that gets you closer to what you want.

Sometimes solving a dating problem means redesigning a lifestyle. Or sometimes it’s simply about stretching your ideas of what’s possible.

“I’ll Date When...”

...my kids are in middle school, high school or leave for college.

...I lose weight.

...I move.

...this project is over.

...life feels less chaotic.

…the season changes.

After years of hearing different versions of “I’ll date when…” I can confirm that whether or not you are in a relationship, life goes on.

Once your kids are in middle school, you might gain a few pounds. Once you’ve lost the weight, your kids might be going off to college, but you decide to move. Once you are in a new city, you are busy learning a new job and taking on a big project.

Life will always be whirlwind in some way.

And you deserve to have the relationship you desire through all the chapters.

In an initial coaching session, we might explore what “ready” actually means, and whether the finish line keeps moving every time you get close to it.

“I’m Too Busy.”

If partnership is one of your biggest goals, it may be time to let your calendar in on the plan.

Part of dating intentionally is being intentional with your time.

Sometimes our coaching session has very little to do with dating and everything to do with creating a life that has room for the things we say matter most.

“I Don’t Even Know If I Want a Relationship.”

Not everyone should pursue partnership simply because society, parents, friends or thoughts you really don’t agree with say they should.

In our initial coaching session, we might explore:

What do you really want?

What kind of life are you trying to build?

How would a relationship add to that life?

What would it require?

Sometimes coaching is about gaining clarity. Whether it leads you toward partnership or in another direction.

“I Lose Myself in Relationships.”

This intial coaching session may ultimately be about:

• Fear

• Approval

• People-pleasing

• Masking

• The desire to be chosen

Somewhere along the way, many of us learned that being “impressive” or “likable” or “easy” on a first date (and then once in a relationship) was more important than being authentic.

Our work together is about helping you show up as you, so you can be seen and chosen for who you really are.

“I Do All the Work.”

Many of my clients are incredibly successful.

They lead teams.

Raise families.

Run companies.

Solve problems all day long.

And those strengths have served them beautifully. Until they start dating.

Some of my favorite coaching sessions are about learning how to do less and leaving room for someone else to contribute.

Your Love Manual Will Guide the Way

Every coaching session eventually leads us back to the same place.

My client’s Love Manual.

Together we will explore your chapters on:

• How you communicate

• How quickly you build trust

• What romance means to you

• How you experience intimacy

• What kind of partnership you want to create

Once these chapters are written, we can build a plan that’s unique to you and rooted in your values and vision of partnership.

So when I get the email prior to a first coaching session that reads…

“I’ve made an appointment for Friday. Is there anything I need to do to prepare?”

The answer will always be no.

You don’t need to prepare.

You don’t need to have the right answers.

You don’t need to know exactly what you want.

You just need to show up.

We’ll start right where you are.

And we’ll figure out what your finish line is and how to get there.

Together.

Welcome to Dear Kara, a weekly column where I address your dating dilemmas, communication challenges and relationship quandaries with honesty, nuance and practical tools you can actually use.

All identifying details have been changed.

If you’d like to submit a question, click the button below. If I select your question, I will send you a personal email with the response (in other words, you don’t need to be a Substack subscriber to submit, so don’t be shy.)

Ask Kara Here

On to this week’s submission!

Dear Kara…

I’m in my 50s and just started dating again. I’ve met someone I really like, but we’re texting constantly. I literally feel like a teenager, texting under the covers until way past my bedtime. I love talking to her, but it’s becoming hard to focus at work, get enough sleep and keep up with everything else in my life. How do I set a boundary without making her think I’m not interested? And…how much texting is actually appropriate when you’re getting to know someone?

-The Bags Under My Eyes Are Impressive

Dear Impressive Bags,

Ha! Before you add a couple of Birkins to your collection, let me start by saying you are not alone. The early days of dating can be incredibly exciting, and the temptation to text like a teenager is strong. However, intensely paced dating combined with a full life of work, family, friends and responsibilities can lead to exhaustion before you know it. And when it does, hearts on fire tend to crash and burn.

Let’s address your easier question first.

How Much Texting Is Appropriate?

The easy answer is: whatever works for the two of you.

There is no one right way to communicate or pace communication, and from your question, I can sense you’ve already started figuring out your own boundaries around what is too much texting.

So the more important question is:

What do you want?

Before your next text sesh, consider:

Do you enjoy texting throughout the day and/or night?

Would you prefer a text or two during the day and a phone call with a specific “goodnight time” at night?

Do you need uninterrupted work hours?

In other words, you’ve established that there’s a connection here. As you grow it, what would help you feel comfortable, energized, respected and still excited to get to know this person?

This is where your healthy boundary begins.

When the Pace Starts to Feel Off

I mentioned you’re not alone in this because I often see my clients get excited about someone new. Like you, they’re human. They are going through the range of emotions that come with new connection, including wondering if the other person is in it as much as they are and trying to match their energy because they’re excited, too.

However, there can come a time when something starts to feel just a little off and you find yourself sacrificing your routines to maintain the pace of connection.

This is such an important point in a budding relationship to acknowledge:

It’s your first opportunity to set a boundary.

Pause and ask yourself:

What do I actually want here?

Important side note: This is a great question to keep in your back pocket anytime anything feels off in a relationship. The answer will bring you clarity. Once you know what you want, we can then discuss how to set a boundary to get what you want.

I know this sounds simple.

But in a brand new relationship, many people skip that step because they’re busy trying to predict someone else’s reaction before they’ve even identified a path forward for themselves.

And that’s where the fear comes in and a letter like yours crosses my desk.

My guess is you aren’t afraid of setting a boundary, but you are afraid of what might happen or change after you do.

“What if she thinks I’m not as interested?”

“What if she thinks I’m not as much fun anymore?”

“What if I screw this up?”

“What if she loses interest?”

Those fears are understandable.

Especially if you’ve tried setting boundaries before and people didn’t respond well. Maybe someone got defensive. Maybe they ignored what you asked for. Maybe they left altogether.

Speaking up is risky, so the temptation to stay quiet (and add to our bag collection) kicks in.

A Boundary Offers Key Information

But here’s the important thing to remember:

Yes, you are dating for the fun, giddiness and excitement. But you’re also dating to discover whether the two of you can build a healthy relationship together.

And as we all know, healthy, lasting relationships have boundaries.

So instead of every boundary being a vibe killer, begin viewing boundary setting as an opportunity for both of you to practice building the kind of relationship you hope to have.

Which leads me to the most important part: the response to the boundary.

How she responds to what you propose gives you valuable information about your compatibility.

Does she say,

Read more

Like how long should a first date be?

Should we do dinner or just drinks?

Does meeting for coffee indicate a friendly or businessy vibe?

How do you end a date when there won’t be a second or express just enough interest if a second date is on the table?

What does appropriate flirting look like these days?

But years of matchmaking and coaching have taught me that none of these questions matter if you don’t make it to the first date to begin with.

A lot can happen prior to getting to know someone in person. As one of my clients put it recently, you might have great “digital chemistry” with someone new. Engaging messaging or fun text banter can really build the anticipation and excitement prior to a first date.

That anticipation is part of the fun.

The challenge is navigating the fine line between fun and an (often accidental) communication fumble.

Unfortunately, there’s a lot that can go wrong in the back and forth before a first date. Assumptions can be made and humor can be misunderstood. Without context, we are all just operating on our own experiences and interpretations.

So, if you want to give that first date the best chance of actually happening, here are five ways people unknowingly kill the vibe before they ever meet.

1. Allowing Your Email to Make the First Impression

Hear me out on this one.

Imagine receiving an email (or a text from a laptop that shows up as an email address in your phone) from someone you’re about to meet.

Instead of seeing a simple version of their name, you see something like:

• ijustusethisfordating@email.com

• cutiepie247@email.com

• jacked69@email.com

Or maybe an email arrives from a random string of numbers because it’s actually being sent from their phone.

While none of these things make someone a bad person or an obviously incompatible match, they do create unnecessary friction. And often doubt.

In a dating landscape full of spam, scams and fake profiles, people are constantly trying to determine whether the person they’re communicating with is the real deal.

A clean email address that includes your name (or a reasonable version of it) communicates something subtle but important:

“I’m a real human being over here.”

Sometimes trust begins with details that seem incredibly small. If you are using a yahoo or hotmail address from over 20 years ago that doesn’t represent who you are now, it might be time to update.

For the record, no judgement - I still have my yahoo address from back in the day, but I do my best not to lead with it. ;)

2. Taking Forever to Respond

No one expects you to be on your phone 24/7 (even though most of us are).

And I get it. We all have careers, friends, family and responsibilities. Ultimately, a full life is attractive.

But disappearing for a week - or worse, two or three weeks - without explanation communicates something whether you intend to or not.

Extended response time sends the message,

“Meeting you isn’t much of a priority.”

If you’re genuinely interested in meeting someone, let your communication reflect that. You don’t have to respond within the hour or even within the same day.

But if life gets busy, do send a quick note.

“I’ve got a packed week, but I’m looking forward to meeting you on Saturday.”

Thirty seconds of communication can be the difference between a first date and no date at all.

3. Your Calendar Is Packed

This one is tough because I know life gets hectic.

But if someone asks you out and your earliest availability is three weeks from now, you might want to ask yourself whether this is actually the right time to be dating.

Dating intentionally requires some capacity and the ability to show up consistently, just like the relationship you eventually want will.

If every invitation feels like squeezing someone into the last remaining fifteen minutes of your calendar, the message you’re sending is clear:

“There’s not a lot of room in my life for you or a relationship.”

If you truly won’t have time until next month, that’s okay.

Maybe that’s the month you start dating.

4. Every Suggestion Becomes a Negotiation

This is a biggie and takes some serious self-awareness.

They suggest grabbing a coffee.

You don’t do caffeine.

They suggest a wine bar.

You’re trying Dry July.

They suggest downtown.

With rush hour traffic, it will take you an extra 20 minutes to get to them.

They suggest Saturday.

You prefer Sunday.

Notice what’s happening here. While none of those preferences are unreasonable, the responses to the suggestions create dead ends. Those dead ends make each suggestion feel like another hurdle someone needs to clear before getting to the first date finish line.

If someone suggests something that genuinely doesn’t work for you, offer an alternative.

Make it easy.

“I’d actually love something active for our first date. How about this place instead?”

Think collaboration instead of negotiation.

Flexibility communicates curiosity and openness. Repeated “I’m not into that”s (without offering an alternative plan) can communicate rigidity and closed-off vibes.

5. Texting Your Way Into a Relationship Before You’ve Even Met

Remember that “digital chemistry” I mentioned earlier? In fun, easy, occasional doses it works, but some people spend weeks texting before ever scheduling a date.

Others schedule the date but continue texting from morning until night beforehand.

Before you know it, you’re envisioning a 5-year plan with someone you’ve never met in person.

The longer you text before meeting, the more likely you are to create a story about who this person is.

They have great comebacks, so they must be witty.

They’re picking up their nephew from school, so they must be great with kids.

They make frequent trips to the suburbs, so they must be ok with leaving the city one day.

Except...

You don’t actually know yet.

You’re filling in the blanks with your imagination.

I’ve watched people talk themselves out of promising first dates simply because they became exhausted by texting.

I’ve also watched people lose interest because they felt like there was nothing left to discover once they finally met.

My advice?

Use the dating app to establish interest and get a date on the books.

Maybe exchange a few fun messages to build anticipation.

Successfully get to the first date, and meet the real person.

Then you can see how they compare to the version you’ve imagined through your phone, before texting about the goldendoodle named Ralph you’d like to adopt together.

The First Date Golden Rule

From the minute you match with someone you are excited about, pause and ask yourself:

Would what I am about to say or do make me want to meet me?

Also try asking that question if you find yourself not taking action.

One of the guiding principles I share with my coaching clients is simple:

So, if you want someone who’s responsive, be responsive.

If you want someone who’s intentional, be intentional.

If you want someone who’s flexible, curious and genuinely excited to get to know you, offer those same qualities first.

Most spend the space between matching and meeting evaluating someone else’s effort.

Are they interested?

Are they communicating well?

Are they making enough of an effort?

But before we ask those questions, we should probably ask ourselves one first:

Am I creating the kind of dating experience I’d want to receive?

Whether we realize it or not, interactions (especially prior to a first date) begin telling a story about what dating us might feel like.

Chemistry may happen across the table on a first date.

But in order to find that out, you’ve got to get to that table first.

So give yourself the best shot by building trust, anticipation, excitement and momentum from the moment you match until the moment you meet in person.

One Final Note

My clients will often say,

“I don’t want to be the one making all the effort from the jump because I fear I’ll be starting off on the wrong foot/setting a precedent/repeating a pattern I don’t want to repeat.”

All fair.

However, when you are meeting someone new, you don’t have their Love Manual and they don’t have yours. I say all bets are off (and all judgements should be set aside) until you get in person and can start communicating how you would like someone to show up in a relationship. If you communicate and they still don’t initiate or show up in a way that feels good to you, then you can consider if you are setting some kind of a precedent or repeating a pattern.

Until the other person understands how you tick, there’s lots to learn and observe - for both of you. Determining true compatibility takes time. Enjoy this exploration.

Here’s to making it to the first date.

And the second…

And the third…

Welcome to Dear Kara, a weekly column where I address your dating dilemmas, communication challenges and relationship quandaries with honesty, nuance and practical tools you can actually use.

All identifying details have been changed.

If you’d like to submit a question, click the button below. If I select your question, I will send you a personal email with the response (in other words, you don’t need to be a Substack subscriber to submit, so don’t be shy.)

Ask Kara Here

On to this week’s submission!

Dear Kara…

I really like someone and I can feel myself getting attached after just a few dates. I think about them more often than I should, check my phone a million times a day and find myself imagining where this could go.

I know I’m getting ahead of myself, but I can’t seem to stop it. I want to be honest, real, vulnerable and open to the possibility without getting so invested so quickly.

How do I slow myself down, yet still show up authentically?

-Already All In

Dear All In,

I started off my week with a coaching session that was very similar to your question.

The first thing I asked my client, and the first thing I would ask you, is: What has happened in the past that causes you to want to slow yourself down now?

For example:

Did a past relationship crash and burn because you went all in too quickly?

Did you find yourself three months in, head over heels, only to realize you and the other person weren’t actually compatible?

Did you ignore important information because you were so excited about the possibility of the relationship?

Whatever the answer, I think it’s worth getting curious about what’s underneath your desire to go all in. Take a peek at your Relationship History or perhaps your Communication and Pacing chapters of your Love Manual.

My Monday client happened to be a realtor, which led to a perfect analogy for the topic at hand.

So, let’s pretend for a moment you’re on the hunt for a new home.

Low Inventory

If you’ve ever been house shopping, you know that in a seller’s market, only a handful of houses may be up for sale, benefiting the sellers. In a buyer’s market, there is more inventory, giving the buyer more options and negotiating power. These markets shift and change all the time due to circumstances largely out of our control.

As a buyer, the state of the market doesn’t necessarily deter your desire to own a home, but you do make adjustments that are within your control.

Perhaps you give yourself a break from house hunting until the market shifts. Maybe you extend your search parameters, rework your priority list or adjust your timeline.

But you don’t give up on your vision completely.

The temptation to give in to a scarcity mindset might creep in, tempting you to buy the first house you like because you’re afraid there won’t be another one.

The market is competitive, you tell yourself.

I’ve already lost out on three houses.

My realtor keeps telling me that inventory is low.

Suddenly, the house you’re standing in doesn’t just feel like a house you like.

It feels like your last chance.

And all of a sudden, you’ve abandoned your original vision and scarcity has set in.

I’ve seen this happen in dating, too. Clients start rushing in, thinking:

What if the dating pool is shrinking?

What if I’m running out of time?

What if this is as good as it gets?

When a scarcity mindset sets in, discernment can go out the window.

You stop asking, “Is this actually the right fit for me?”

And start asking, “How quickly can I make this work and lock it down?”

The risk is that you achieve the goal of buying a house or finding a partner, only to realize days, months or years down the road that you abandoned your original priorities and vision in the process.

Bottom line: Just because you haven’t found the right house yet doesn’t mean you should buy the wrong one because you’re afraid the market is running out of inventory.

So take your time.

And to be fair, you may have found the one. Enjoy the intense “like” while giving yourself enough space and time to see if that “like” is enduring before locking yourself in.

But the Kitchen Is Perfect

Anxiety, or an anxious attachment style, can create a different kind of urgency.

You find a house with the kitchen you’ve always dreamed of and you’re terrified you’re going to lose it.

So you hold on tight.

You start convincing yourself that the tiny yard is fine.

You can deal with the long commute.

The neighborhood isn’t exactly what you wanted, but maybe you’ll get used to it.

You can picture yourself having your morning coffee, cooking your favorite recipes, relaxing and entertaining in that kitchen.

And because you’re afraid of losing it, you start overlooking the things that don’t actually work for you.

This happens in dating and relationships, too.

You like someone so much and crave the feeling of attachment so deeply that you start negotiating with yourself about the things that don’t feel right.

The communication is inconsistent, but you tell yourself they’re just busy.

You want more affection, but convince yourself you shouldn’t need it.

You have different values or visions for the future, but you think maybe one of you will change.

You don’t feel entirely comfortable being yourself, but you’re so afraid of losing the relationship that you hold on tighter.

Your anxiety goes through the roof, and you think the only way to quiet it is to quickly call, “All in!”

Whether or not the relationship is actually working for you.

Bottom line: Step back. Zoom out. Look at the big picture.

You’re not going to sleep in your kitchen.

And if the plumbing doesn’t pass inspection, you won’t be able to use your perfect kitchen at all.

When you experience intense emotions, even if they are really good feels, remind yourself to zoom out and look at the house, or the person, as a whole.

Equally consider the parts that don’t feel perfect before letting anxiety make the call for you.

When “Buy a House” Is the Next Goal on Your List

The third most common reason I see clients want to go all in quickly is good old-fashioned impatience.

This is often the easiest to detect because it shows up in other areas of my clients’ lives, not just in their love lives.

Case in point...

The goal: Buy a home.

You have been house hunting for weeks.

You’re tired and you want to be done.

You simply want to check the box.

You walk into the next house and think, “Good enough.”

When it comes to finding a relationship, it looks a little something like this.

The goal: Get married.

You want to be done dating.

You want to stop swiping, going on first dates and wondering if this person could be the one.

Find someone. Check.

Get into a relationship. Check.

Stop dating. Check.

But the desire to reach the end goal can override your discernment.

You may be so focused on finally being “done” that you forget to ask whether you actually want to live in the house you’re about to sign off on.

Bottom line: Make gathering enough information to determine real compatibility the box you check before you check the “all in” box.

So, How Do You Avoid Buyer’s Remorse?

You can’t control the housing market. You can’t know exactly when the right house will come along. But you can make sure you don’t let scarcity, anxiety or impatience talk you into buying a house you don’t actually want to live in.

Here’s how:

Read more

First, a 53-year-old client shared that she is dating someone who describes himself as kinky. This is a first for her and she is showing up to this relationship curious, open and ready to learn. In her previous long-term relationship, her sex life was fulfilling, but shall we say...tended toward a scoop of vanilla?

Now she’s getting a taste of desserts she never realized were on the menu.

She’s adding to the Romance, Sex and Intimacy chapter of her Love Manual at warp speed. She’s both loving it and acknowledging that it’s a lot of new information to sort through while trying to stay present in the exploration.

Another client is having a different sexual experience.

He shared, “The beginning of our relationship felt effortless. We couldn’t keep our hands off each other. It’s been six months and real life has started to settle in. I’m wondering how we keep that part of our relationship alive and healthy.”

Different people. Different stages of dating. Both reaching the point when a conversation about sexual alignment is on the table.

Gulp.

Where Do You Even Start?

If you’ve been following along here at The Love Story Lab, you know that I believe every person should take the time to write their own Love Manual, a guide to how they love, communicate, repair conflict, build a life and create partnership.

I’ve found that prior to getting into a relationship, it’s pretty easy for clients to talk about their chapter on Attraction and Chemistry.

“I’m so attracted to curves.”

“Chivalry will get you everywhere.”

“I love when someone maintains eye contact and laughs easily.”

“Classic Ray-Ban aviators + a suit? Yes, please.”

However, when it comes to the chapter on Romance, Sex and Intimacy, things tend to get a bit more nuanced and, for many, harder to communicate. Especially once the novelty of a new relationship turns into a deeper, more familiar dynamic.

For some people, the sex section of their Love Manual practically writes itself.

For others, it’s a blank page with a blinking cursor.

Perhaps it’s written in your Family and Upbringing chapter that discussing sex was taboo. Maybe your Relationship History chapter taught you what your partners liked but not what you liked. Maybe you’ve had very little experience. Maybe you’ve had plenty of experience but never stopped to question why certain things felt exciting while others, well...didn’t.

When it comes to figuring out what we want from sex and, subsequently, how to communicate it, one of the most helpful frameworks I’ve found comes from somatic sexologist Jaiya. She developed the Erotic Blueprints™ framework, which offers a language for understanding what creates arousal, connection and pleasure.

Similar to the Five Love Languages, Jaiya describes five erotic languages, acknowledging that not everyone experiences the same brand of pleasure. Understanding that your own may be different from your partner’s can be extremely helpful when navigating new sexual territory or creating a long-term plan for a healthy and fulfilling sex life.

Or simply as a tool to open up a conversation about sex.

In my experience, many people have never considered that what turns them on might be fundamentally different from what turns on their partner.

That knowledge alone is incredibly freeing.

Five Different Erotic Experiences

So what are the five Erotic Blueprints and how do they differ from one another? Here’s a brief overview. For more detailed information and to discover your own Erotic Blueprint, please visit Jaiya’s work here.

Sexual

If your blueprint is Sexual, the physical acts of sex are your erotic cup of tea. You tend to think, “Let’s have sex!” and the next thing you know, you’re getting the job done. You like to go straight for the cash and prizes. No beating around the bush with this blueprint.

For you, sex is fun, easily accessible and you enjoy taking the physical path to orgasm.

Sensual

If you have a Sensual blueprint, circumstances and environments that engage and delight your senses are the keys to your pleasure.

Music can put you in the mood. Lighting can create an enticing ambiance. Certain scents transport you. Textures tempt you.

Anticipation and slowing down often matter just as much, if not more, than the physical sexual activity itself.

Energetic

For someone with an Energetic blueprint, a deep emotional, spiritual and physical connection does the erotic trick. Often, touch isn’t the name of the game. Instead, a transcendent experience and exchange of energy is.

Kinky

Those with a Kinky blueprint find excitement in novelty, psychological play, power dynamics, exploration or experiences that feel taboo. Kink exists on a wide spectrum and isn’t defined by any one activity.

However, if on-demand orgasms sound erotic to you, this might be a clue to your unique, and kinky, blueprint.

Shapeshifter

The Shapeshifter blueprint does it all and enjoys it all done to them. The Shapeshifter welcomes variety and often resonates with aspects of all of the other blueprints, adapting to different experiences and partners with ease and enthusiasm.

When I first heard Jaiya speak about the five Erotic Blueprints, it was like fireworks went off in my brain.

This information belongs in one’s Love Manual.

My second thought was:

What a great springboard for opening up conversations about sex.

Many assume sexual compatibility is either something you have...

...or you don’t.

In reality, many people simply don’t have a shared vocabulary.

Sometimes when sex isn’t clicking right away or, once the “honeymoon phase” has worn off, you find yourself wondering, “Uh oh, is this it?” All is not lost. You simply may not fully understand each other’s Erotic Blueprints just yet.

Chemistry, Compatibility and Conversation? Oh My.

Ah, early dating.

A time when everything is new. Everything feels exciting. You can’t wait to see each other. The chemistry and attraction, often amplified by the newness itself, are undeniable.

Then something happens.

Work gets busy. Life gets stressful. You trade talking, texting or having sex into the wee morning hours for a few extra hours of sleep.

The novelty naturally fades.

Sometimes couples assume this means the relationship is broken or doomed.

I don’t.

I think it’s the moment when communication and conversation become more important than the initial attraction and chemistry that brought you two together.

It’s the perfect time to fill out your chapter on sex by asking yourself:

What helps me feel desired?

What helps me relax?

What turns me on emotionally?

Physically?

Mentally?

What makes me shut down?

And then, the equally important part.

Start a conversation with your partner that begins with, “Have you ever heard of an erotic blueprint?”

A Quickie for Your Consideration

Another concept that’s been helpful for my clients is understanding the difference between spontaneous desire and responsive desire, a distinction explored by sex researcher and author Dr. Emily Nagoski.

Spontaneous desire means sexual interest seems to appear on its own. You think about sex and immediately, you are ready to go!

Responsive desire means desire develops after a bit of build-up, which can look like conversation, affection, flirting, relaxation or physical touch other than going straight for the cash and prizes. Interest builds in response to the moment rather than arriving before it.

One isn’t better than the other. They’re simply different.

And when two people don’t know this, they can create stories about one another.

“If they wanted me, they’d initiate.”

“They’re just not attracted to me anymore.”

“They never think about sex.”

Often, none of these stories are true.

One partner may simply experience responsive desire while the other experiences spontaneous desire.

Understanding the difference can replace frustration with curiosity.

For more on this topic, Dr. Emily Nagoski is a wonderful resource as a researcher, author and podcaster. You can explore her work here.

So, What Works for Me?

That’s the question your Love Manual chapter on Romance, Sex and Intimacy is designed to answer.

The more clearly you understand your own section on sex, the more generously you can invite someone else into it.

And the ability to open up that conversation?

In my experience, that’s where real, lasting sexual intimacy begins.

If you need some support getting the conversation started, you know where to find me.

Welcome to Dear Kara, a weekly column where I address your dating dilemmas, communication challenges and relationship quandaries with honesty, nuance and practical tools you can actually use.

All identifying details have been changed.

If you’d like to submit a question, click the button below. If I select your question, I will send you a personal email with the response (in other words, you don’t need to be a Substack subscriber to submit, so don’t be shy.)

Ask Kara Here

On to this week’s submission!

Dear Kara…

I feel like I’m always the question asker. The conversation carrier. I’m the one learning everything about the other person. They’ll happily answer my questions, but they rarely ask me anything in return. By the end of the date, I know about their childhood, their job, their ex and their favorite vacation, but they barely know anything about me.

Why does this keep happening? Is it nerves? A lack of social skills? Or am I just attracting self-centered people?

More importantly, what should I do when I’m sitting across from someone who doesn’t seem curious about me?

—Officially Out of Questions

Dear Out of Questions,

If dating were the World Cup, you’d be leading in the category of Questions Asked:

You: 17

Them: 1 (And it was “Are you ready to order?”)

It’s a game that hardly has you screaming “GOOOOOOOOOOOAL!” when you score #18.

It sounds like you’ve mastered running the perfect date, for the other player.

You’re likely keeping the conversation alive. Thinking of the next question. Preventing awkward silences. Learning everything there is to know about the person across the table.

Meanwhile, they’re happily answering every question you ask without ever inquiring about you.

The good news is that there are a few things you can try to turn the tide of the conversation. But first, it’s worth considering why someone might not be asking many questions in the first place.

They could be nervous and filling every silence with words.

They may genuinely think they’re connecting by sharing lots of stories.

Some people grew up in families where conversations looked more like storytelling than turn-taking.

Others have never realized that asking thoughtful questions is part of making someone else feel seen.

And yes, sometimes the explanation is the bane of every question asker’s existence.

Some people are so focused on being interesting that they fail to be interested.

The challenge is that, early on, those can look remarkably similar. And all you know for sure is that the conversation feels like a solo sport instead of a team effort.

One of my favorite ways to turn the tide is to test the waters before you feel like you’re drowning in never-ending stories.

Read more

As I’ve been writing their ceremony, I’ve found myself thinking not only about their origin story, but about how so many of the relationships I’ve had the good fortune to witness began.

Most started with some kind of hiccup.

A miscommunication.

Mismatched pacing.

A mix-up about where someone was supposed to be or when.

An unforeseeable circumstance that led to a canceled date.

Sometimes there was almost no interaction at all.

Which has me thinking...

We’ve been conditioned to evaluate:

Is this it?

Is this my person?

Do I feel the spark?

Did they ask enough questions?

Were they funny enough? Serious enough? Attractive enough? Ambitious enough?

Can I see myself making some kind of lifelong commitment to this person?

We’re trying to predict an entire lifetime with someone from a ninety-minute conversation.

Yet when couples stand at the altar, they almost never begin their vows by talking about how perfect the first date was.

Instead, they tell stories.

Funny stories.

Stories about awkward beginnings.

Stories about chance meetings that almost didn’t happen.

Stories about meeting each other, then going on with their lives for years before finding their way back to one another. Can you tell this one is familiar?

We judge first dates by criteria that almost never make it into wedding vows.

Even fairy tales don’t start out as fairy tales.

The Tale of He Knew First

My best friend’s soon-to-be husband knew before she did.

He saw something special early on.

She wasn’t quite as certain. She was taking her selection process very seriously.

He stayed steady while she continued figuring out her own heart. Eventually she caught up. In fact, his grounded response to her vulnerable, “I’m not quite there yet,” helped her get there much sooner than she ever imagined she would.

This weekend they’ll exchange vows.

Had either of them bolted when they discovered their mismatch in readiness, this weekend would look very different.

The Tale of My Own Existence

If it weren’t for a scheduling conflict, I wouldn’t be writing this post.

My mom is a twin. Originally, her sister was supposed to go out with my dad.

Days before the date, my aunt got “a better offer,” as my mom tells the story.

So she sent my mom on the date with my dad in her place.

And thus, I’ve lived to write about it.

The Tale of My Own Love Story

When I met my wife, and to be clear, I had absolutely no idea she would become my wife, at our mutual friends’ wedding reception, I was in another relationship and had what I call “relationship blinders” on.

While I remember being perfectly polite, Jen remembers me as chilly, at best.

It wasn’t until three years later, when I was single, that our mutual friends of twenty years, convinced we should be together, reintroduced us. And we gave it a shot.

And by “gave it a shot,” I mean we spent several wonderfully awkward movie and dinner “dates” trying to figure out what, exactly, was happening.

Today, movie dates are one of our favorite traditions. What started as uncertainty became rainy afternoons in reclining chairs sharing loaded tots.

Had we not continued showing up without knowing exactly where things were headed, I can’t even imagine what my life would look like today.

The Tale of Misleading Body Language

I introduced one of my favorite couples during a strategically planned dinner party.

And by “strategically planned,” I mean I had a strong hunch these two were going to hit it off, so I hosted a low-stakes chili night potluck, invited a handful of guests and decided to let things unfold naturally.

As a huge blow to my matchmaking ego, they barely spoke all night.

They hardly looked at each other.

That evening I went to bed thinking, Maybe I’m completely delusional and have no business doing this matchmaking thing.

The next morning I woke up to two separate emails.

Each asked the exact same question.

“Could I have her number?”

They had both been incredibly interested.

And they had both been incredibly nervous.

Imagine if any of us had stopped at first impressions.

Instead, they both found the courage to reach out afterward.

Today they’re married.

And my faith in my matchmaking abilities survived.

We’ve Been Trained to Expect Instant Certainty

In the spirit of The Summer of What Ifs...

What if the awkward first meeting eventually becomes part of your wedding vows?

What if the person you described as “nice, but I didn’t really feel a connection,” simply needed another hour for you to discover a quality you found incredibly attractive?

What if the person who didn’t give you butterflies at first gave you something greater?

Peace.

Steadiness.

Consistency.

Safety.

And what if those things eventually created the butterflies?

We live in a time where almost everything arrives immediately.

Need ¼ inch white ribbon for hanging wedding lanterns?

Amazon can have it on your doorstep tomorrow morning between 7am and 11am (as it turns out).

Want the perfect wedding bangers playlist?

Spotify produces several simply by typing in “Weddi.”

Need a little liquid courage before officiating a wedding?

There’s probably an app for that too.

We’re surrounded by convenience, certainty and instant gratification.

I have a strong suspicion we’ve brought those expectations into dating.

If there’s an awkward silence...

If conversation doesn’t flow effortlessly...

If there isn’t immediate chemistry...

If one answer leaves us wondering...

We assume we’ve seen enough.

We’re not wasting time.

Next.

But people aren’t Amazon packages, playlists or cocktails. They’re human beings. Complex ones at that. And complexity takes time, patience and curiosity to discover.

Consider Your Story

I often ask clients:

Could someone fully understand you after one date?

Could they know your resilience?

Your humor?

How deeply you love your people?

How you’ve changed over time?

The traditions you hope to build someday?

Of course not.

You’re far more interesting than one date.

And so is the person sitting across from you.

Before You Say “I Don’t”

The next time a first date doesn’t completely knock it out of the park, ask yourself one question.

I’m not suggesting you ignore red flags.

If someone is disrespectful, dishonest, unsafe or fundamentally misaligned with the life you want, trust yourself.

But if the biggest issue was that the conversation wandered...

Or one of you was nervous...

Or one of you simply liked the other a little sooner...

Or there were a few awkward pauses...

Leave a little room for curiosity.

Leave a little room for surprise.

Imagine Your Future Wedding Vows

Before you decide there won’t be a second date, imagine your future self.

You’re standing at the altar. The room is full of people who love you. You’re reading your vows. What if they began like this:

“When I first met you, I just thought we would be really good friends.”

“After our first date, I didn’t think I’d hear from you again.”

“I almost let one awkward evening convince me we weren’t meant to be.”

“Our first date was so confusing that I almost didn’t agree to a second.”

The couples I know don’t laugh about perfect first dates. They laugh about the hiccups. It’s those hiccups that make their story uniquely theirs.

And someday, if you’re open to it, your favorite love story could begin with the words:

“When I first met you, I had absolutely no idea you would become my person.”

Trust me.

I’ve seen this story unfold more times than I can count.

Welcome to Dear Kara, a weekly column where I address your dating dilemmas, communication challenges and relationship quandaries with honesty, nuance and practical tools you can actually use.

All identifying details have been changed.

If you’d like to submit a question, click the button below. If I select your question, I will send you a personal email with the response (in other words, you don’t need to be a Substack subscriber to submit, so don’t be shy.)

Ask Kara Here

On to this week’s submission!

Dear Kara...

I matched with someone on a dating app a few weeks ago. Our conversations were easy, funny and the banter felt different from most conversations I’ve had on the apps.

Then something completely unexpected happened.

A friend offered me a ticket to a World Cup game, but I had less than 24 hours to pull it all together. I ended up booking flights and a hotel, then turned the trip into a vacation with a few friends. Between the travel and wanting to be present, I stopped checking the apps altogether.

When I got home, I was buried catching up at work. I’m finally coming up for air and I keep thinking about the guy with the good banter.

The problem is...it’s been almost three weeks.

I feel guilty for disappearing. I know ghosting doesn’t feel good, and I don’t want him to think I wasn’t interested because I actually was.

Is it too late to message him? Or did I miss the window?

- Hoping It’s Not Too Late

Dear Hoping,

Good news. It’s never too late to revisit a conversation.

Not on a dating app.

Not after a first date.

Not even after a few dates.

Last-minute trips happen. New jobs happen. Family emergencies happen. Overwhelm happens.

Life happens.

Sometimes you have no control over the circumstances, whether they’re challenging or once-in-a-lifetime opportunities, like the chance to attend a World Cup game. But what you do have control over is how you show up when you want to revisit a conversation.

Here’s how.

First, Figure Out the Feelings

Before you send any message, take a minute to notice what you’re actually feeling. You’ve already articulated exactly how you feel.

You’re afraid you missed out.

You feel guilty for ghosting.

And underneath all of that, you’re hopeful enough about the connection that you want to reach back out.

The fact that you know disappearing probably didn’t feel very good for the other person tells me you have empathy. Empathy is a perfect place to begin.

When we skip this step, we tend to send messages that sound like excuses.

“I’ve just been so busy.”

“Things have been crazy.”

“I haven’t had time to check the app.”

Maybe those things are true.

But they don’t acknowledge two important things: your genuine feelings and the impact.

One of the most important chapters of your Love Manual is Conflict and Repair. Early on in my Substack journey (and by the way, can you believe this is post #50?!?), I wrote about why conflict isn’t the problem - avoiding repair is.

If you haven’t read it yet, it’s a great companion piece to today’s question because this is simply repair before you’ve even had a first date.

But for today, let’s talk about what repair can actually sound like when you’ve gone MIA for a few weeks.

Read more

Together, we’ve explored their Love Manual chapters on Family and Upbringing, Relationship History, Values, Lifestyle and Vision of Partnership to determine what feels right for them.

Over the years, I’ve found that the biggest obstacle when it comes to long-distance dating might not be the miles.

It’s often been the story my clients have been telling themselves about the miles.

If you’ve been wondering, Is long-distance love really possible? ask yourself...

1. If I Knew My Person Lived Somewhere Else, Would I Go?

When I ask,

“If you knew with absolute certainty that your soulmate lived in another city, another state or even another country, would you refuse to meet them?”

the answer is almost always instant.

“Of course not.”

“I’d book a flight tomorrow.”

“I’d absolutely want to meet them.”

And then, often in the very next breath of the same conversation, I’ll hear:

“But I would never date someone long distance.”

“If I can’t see someone in person several times a week, it’s just not going to work.”

“I don’t date anyone who lives more than thirty minutes away.”

Somewhere, between crossing an ocean for the right person and refusing to drive forty-five minutes for a first date, something doesn’t quite add up.

I’m not suggesting everyone should pursue a long-distance relationship. There are absolutely people who know, based on the life they want or have built, that it isn’t the right fit. However, even people with restrictive custody agreements or location-specific careers may discover someone who is willing to travel to them for the right connection.

Sometimes I wonder how many people are ruling out long-distance dating from a place of thoughtful preference and how many are ruling out the possibility from a place of protection.

2. Am I Avoiding Long-Distance Opportunities to Avoid Past Hurts Happening Again?

I’ve noticed that many people who confidently say they’ll never date long distance have a story behind that decision.

Maybe they invested months, or years, in someone who never intended to close the distance.

Maybe they were always the one earning points and spending miles to see the other.

Maybe communication slowly faded and eventually broke down.

Maybe they were heartbroken.

Those experiences are real. They deserve to be honored and they leave a lasting impact.

This is where I often encourage clients to revisit their Relationship History chapter. Not because the past should dictate the future, but because it often explains why certain fears or preferences exist in the first place.

There’s an important distinction worth considering.

That relationship didn’t work.

That doesn’t automatically mean long-distance relationships don’t work.

Just like if one relationship ended because of poor communication, we don’t swear off communication forever.

Geography often gets blamed for problems that were actually about commitment, compatibility, honesty, effort or timing.

Sometimes “long-distance doesn’t work for me” is absolutely true. Other times, it’s simply a past hurt speaking. There’s value in acknowledging the difference.

3. What’s More Important to Me: Convenience or Compatibility?

Sometimes we confuse convenience with compatibility.

Living ten minutes away makes someone convenient.

It doesn’t make them emotionally available, kind, curious, funny, self-aware, trustworthy or capable of building a healthy partnership.

When people tell me they’re looking for “their person,” they rarely describe someone based on geography.

They tell me they want:

• Someone they can laugh with.

• Someone who matches their energy.

• Someone who shares their values.

• Someone who understands them.

• Someone who chooses them every day.

Notice what doesn’t come up. Zip code. Driving distance. An arbitrary fifty-mile radius.

Those are logistical details, not relationship qualities.

This is one of the reasons I encourage people to revisit their Values chapter. When you get crystal clear on the qualities that truly matter, convenience often becomes exactly what it is: a bonus, not a requirement.

The more important it is to find one extraordinary person to build a life with, the more important it becomes not to unnecessarily shrink your search.

I mean, what if your person is at mile fifty-one?

4. Given What I’m Looking For, How Big Is My Current Dating Pool?

When I was a professional matchmaker, I worked primarily with LGBTQ+ clients. Their wish lists looked remarkably similar to those of my straight clients:

• Kind

• Funny

• Emotionally available

• Adventurous

• Family-oriented

• Great communicator

The difference wasn’t what they wanted.

It was the size of the dating pool (at the time, only 7% of the U.S. population identified as LGBTQ+).

Once we narrowed that pool by age, relationship status, compatibility and location, it became remarkably small, especially for people living outside major metropolitan areas.

That meant we had to become creative.

We couldn’t afford to dismiss someone simply because they lived in another city or another state.

Instead, we widened search parameters.

We focused less on proximity and more on compatibility.

And it worked.

Expanding the search created introductions that never would have happened otherwise.

It also reinforced something I’ve believed ever since.

If your goal is finding a truly compatible partner, not simply someone who is geographically convenient, the most effective strategy is giving yourself more opportunities to meet more compatible people.

That’s also a Vision of Partnership conversation.

If your vision is to build a meaningful relationship with one exceptional person, it may be worth asking whether your current search area reflects that vision or unintentionally limits it.

5. In General, Do I Rule Possibility In or Out?

One of my favorite coaching philosophies is simple:

Not forever, but long enough to gather real information.

Maybe that’s saying yes to someone two hours away.

Maybe it’s matching with someone who lives in another state.

Maybe it’s taking one weekend trip before deciding it could never work.

The same philosophy applies to so many things in dating. Ages. Heights. Careers. Relationship histories.

If we eliminate everything unfamiliar before we’ve experienced it, we’re making decisions based on assumptions instead of real-time evidence.

I’d much rather you gather the evidence and then decide than miss the opportunity altogether.

This is often where I encourage clients to revisit their Family and Upbringing chapter.

Were you raised believing love should always happen close to home?

Did everyone around you marry someone from the same neighborhood, the same school or the same town?

Or did you grow up believing relationships should fit into one very specific picture?

There’s nothing wrong with those influences.

But it’s worth asking whether they still fit the life you’re trying to build today.

One more time for those in the back:

Some of the happiest couples I know would never have predicted each other on paper prior to meeting.

6. What If the Relationship Became the Adventure?

When I ask people what they want in a partner, one answer comes up over and over again.

“I want someone who loves to travel.”

My clients dream about weekend getaways, exploring new cities and experiencing different cultures.

They want to collect memories together.

Whenever I hear that, I think:

Why not let the relationship itself become part of the adventure?

Long-distance dating naturally creates experiences many ultimately desire.

This is where we revisit my client’s Lifestyle chapter.

Sometimes we discover they’ve assumed that a healthy relationship means seeing each other every evening.

Other times, they realize what they truly value is independence paired with shared experiences, flexibility or adventure.

And by now you know me.

I’ve always believed we date more than people:

• We date jobs.

• We date cities.

• We date neighborhoods.

• We date lifestyles.

• We date possibilities.

Every relationship introduces us to another version of life.

And if we are lucky, every relationship introduces us to another version of ourselves.

7. What Would Have to Be True for Me to Be Open to Long-Distance Dating?

I’m not going to pretend long-distance dating doesn’t come with challenges.

It requires intentional communication.

Planning.

Trust.

Patience.

Conversations about expectations.

Two people who are equally committed to overcoming obstacles together.

But healthy relationships require those things anyway.

Long-distance dating simply asks couples to practice them earlier because you can’t rely on convenience.

You can’t substitute proximity for communication.

You actually have to talk. Make plans. Ask yourselves where this is headed.

Ironically, many long-distance couples develop incredibly strong communication skills because distance doesn’t allow them to coast.

People often ask me,

“So...how do you make long-distance work?”

My answer is simple.

Both people have to be open to making it work.

That’s it.

Not one person dragging the other.

Not one person secretly hoping the other will eventually move.

Not one person doing all the traveling.

It takes mutual willingness.

When two people genuinely want to build something together, they become remarkably creative.

They alternate flights.

They schedule FaceTime dinners.

They spend weekends together.

They work remotely from each other’s cities.

They meet in the middle.

Eventually, they make thoughtful decisions about where and how they want to build a shared life, whether that’s relocating, splitting time between two places or choosing an entirely new city together.

So instead of asking,

“Would I ever date someone long distance?”

I encourage my clients to ask,

“What would have to be true for me to be open to it?”

That’s where the Love Manual becomes so valuable.

We revisit the Relationship History chapter to separate old hurts from current reality.

We explore Family and Upbringing to understand where our beliefs about love first took shape.

We return to Values, Lifestyle and Vision of Partnership to determine what truly matters and what may simply be habit, fear or assumption.

The goal isn’t to convince yourself that long-distance dating is right for you.

The goal is to make the decision consciously.

From a place of clarity rather than fear.

From a place of possibility rather than protection.

After all...

If your person happened to live somewhere else today, would you really want geography to be the reason your story never started?

Welcome to Dear Kara, a weekly column where I address your dating dilemmas, communication challenges and relationship quandaries with honesty, nuance and practical tools you can actually use.

All identifying details have been changed.

If you’d like to submit a question, click the button below. If I select your question, I will send you a personal email with the response (in other words, you don’t need to be a Substack subscriber to submit, so don’t be shy.)

Ask Kara Here

On to this week’s submission!

Dear Kara...

The last few months have been absolute chaos at work. I’ve been putting in long hours, traveling and honestly didn’t have the bandwidth to even think about dating.

One night I got on Grindr looking for exactly what everyone assumes you’re looking for on Grindr: a little fun, no expectations, no pressure. I started chatting with a guy who only had a chest photo on his profile. We clicked immediately. The conversation was funny and easy, so we met up.

One thing led to another, exactly as originally planned.

The surprise came afterward.

We texted the next day and about a week later decided to actually go out. We grabbed dinner, talked for hours, laughed a lot and somehow it felt different.

We’ve only been on two dates, but now I’m realizing something I did not expect.

I think I actually really like this guy.

Now I don’t know what to do.

Do I keep texting him the same flirty, sexy messages we’ve been sending? Do I ask him out again and see where this goes? Do I tell him I’m interested in getting to know him better? Am I reading too much into this after only two dates?

Basically, what happens when the summer fling starts becoming a thing?

—Unexpectedly Interested

Dear Unexpectedly Interested,

Read more

This week marks one year since I launched The Love Story Lab.

It also marks six months since I hit “publish” on my very first Substack post.

While neither anniversary comes with fireworks or a parade, I can’t help but pause and acknowledge the gifts of the past year.

I encourage my clients to celebrate progress, not just outcomes. We celebrate when the dating profile goes live, when the first message is sent and when the vulnerable question is finally asked.

We delight in the anticipation of the first date, setting healthy boundaries and staying true to ourselves even when it would be easier not to.

As I’ve reflected on this first year, I found myself smiling and realizing something.

Building a coaching business has felt an awful lot like dating.

Apparently, the advice I give my clients wasn’t just for them. It was for me, too.

You have to show up before you know whether it’ll work.

One year ago, I left a full-time job I loved.

I invested in a new website and will always be grateful to my talented sister who built it.

I started writing a book as a way to share everything I’ve learned from nearly a decade as a professional matchmaker and dating coach.

I wrote my first Substack post.

I shared my posts on Facebook, Instagram and LinkedIn.

I met with my coaching peer group, who I lovingly call my “cheer group,” every week.

I attended Sessions Live 2026 and had the opportunity to be in the same room as Esther Perel, Dan Savage and more therapists and coaches than I had ever seen gathered in one place.

None of those things came with guarantees.

Just like dating.

You create the Hinge profile.

You send the messages.

You agree to first dates.

And second dates.

You ask the questions.

You don’t do these things because you’re certain they’ll work. You do them because you can see the vision and you’re willing to explore every avenue to make it a reality.

This year reminded me that effort isn’t a guarantee of success, but it is the necessary price of admission.

Sometimes figuring out what doesn’t work is just as valuable as figuring out what does.

Some posts get likes and comments.

Some don’t.

Some Substack posts resonate.

Some don’t.

Not every chapter I write belongs in the book.

Some things have taken much longer than I expected. Other ideas I’ve happily set aside because they no longer felt like the right direction.

I’m grateful for all of it because every “Mmm... probably won’t do that again,” every late-night rewrite and every pivot gave me information I didn’t have before.

It’s exactly what I tell my clients after a first date that doesn’t turn into a second.

That date wasn’t a failure or a waste of time.

Maybe it clarified what you’re looking for.

Maybe it revealed a pattern in how you show up.

Maybe it simply made for a really good story.

Dating and building a business aren’t pass or fail. They aren’t simply yes or no. Both offer a collection of data points that gradually lead you toward what feels most aligned.

You never know why someone is entering your life.

This may be my favorite lesson from the past year.

One of the greatest joys of starting The Love Story Lab has been reconnecting with people from my matchmaking years and even earlier.

Some are people I only spoke with once or twice.

Others I hadn’t talked to in years.

And yet they’ve referred clients, offered encouragement, celebrated wins, shared my work and reminded me that people are often more generous than we expect.

Not every person you meet is meant to become your partner.

Some become lifelong friends.

One may introduce you to someone you’ll love.

Some show up years later with an unexpected opportunity.

Sometimes the reason you meet someone isn’t revealed until much later.

That’s one of the reasons I encourage clients to show up authentically and treat people well, even when, and especially when, the romantic connection isn’t there. You simply never know what role someone may play in your story or in which chapter they will appear.

One of my favorite pieces of dating advice has become one of my favorite pieces of life advice:

Prepare to be surprised and delighted by what you don’t yet know or couldn’t possibly conceive for yourself until it happens.

A year ago, I couldn’t have imagined some of the people who would become champions of my work. I couldn’t have predicted which conversations would turn into referrals, which ideas would resonate or how this little community on Substack would begin to grow.

If we’re willing to stay open, life has a wonderful way of introducing possibilities we never would have thought to put on our own vision board or our partner wish list.

Pivoting isn’t failure.

I thought I’d be further along with my book by now.

Instead, I’ve rewritten chapters, changed directions and realized that some ideas simply need more time to grow.

I’ve even accidentally deleted just over 20,000 words. That was a fun day.

I’m human. So sure, I’d love to be planning my book tour and speaking engagements for the fall. But there’s likely a reason I’m not there yet.

Perhaps I’m meant to turn each chapter of How to Write Your Love Manual into a workshop, workbook, seminar or learning community.

I’ve learned that changing course isn’t giving up.

I’m responding to what I’ve learned along the way.

Dating is strikingly similar.

If one approach or type isn’t bringing you closer to the relationship you want, you’re allowed to adjust.

Growth isn’t staying committed to a strategy that isn’t serving you.

Growth is having the courage to evolve.

Relationships and coaching are wonderfully bittersweet.

One thing I wasn’t fully prepared for this year is how genuinely fulfilled I would feel by the relationships I built with my clients.

I can’t count the number of times I’ve smiled ear to ear after getting an email with photos of clients living their best lives on vacation, wearing a new outfit for a first date or spending time with someone they were genuinely excited about.

Each time I’ve received a text reporting “I love yous” have been exchanged, families have been met or sleepovers have happened, I let out an audible, “Eeeee!”

I have an equal amount of gratitude for the sessions when my clients decided a relationship wasn’t working, dating burnout was at an all-time high or they simply needed help figuring out how to have a hard conversation.

Every coaching relationship is different, but each one is built on trust.

I never take for granted the opportunity to walk alongside my clients through their hopes, fears, excitement, heartbreak and growth.

Then, ideally, something wonderful happens.

My clients feel strong on their dating legs.

They’re in the relationships they want.

Or they decide to take a break from dating.

And for the time being, our work together is complete.

Which, of course, is the goal.

It’s also a little bittersweet.

Just like some relationships are wonderful but you know they must come to an end, I experience that, too.

Thankfully, it’s never long before another person arrives who needs someone in their corner.

Build a whole life, not just one part of it.

This year wasn’t just about building a business.

Yes, I’m celebrating one year of The Love Story Lab.

Yes, I’ve spent six months writing here on Substack.

Yes, I’ve coached incredible clients, had countless conversations about love and relationships, started writing a book, deepened relationships with referral partners and reconnected with people who have cheered me on in ways I never expected.

But that’s not the whole story.

I started The Love Story Lab for many reasons: to fulfill my coaching vision, spread my wings professionally, challenge myself and create the freedom to build both my schedule and a client roster that felt truly aligned.

But this year I also spent two weeks in Scandinavia. I simply blocked off my calendar and went.

I’ve celebrated weddings and will be officiating my best friend’s wedding in a couple of weeks.

My sister and one of my dearest friends surprised me at our annual Jen Den Christmas party in a way I’ll never forget.

I met a new friend.

Jen and I enjoyed “second rounds” (afternoon iced lattes), I got “jacked” (okay, I just started lifting weights) and I’ve continued checking fun things off my 2026 bingo card (like driving a golf cart).

I’ve tried to make memories alongside the milestones.

And I’m so grateful I did.

I’m convinced that one of the biggest mistakes we can make, in dating, in business and in life, is believing life doesn’t really begin until we reach the next milestone.

Until we find the relationship.

Until we get married.

Until we launch the business.

Until we finish the book.

Life isn’t waiting for us at the finish line.

It’s happening right now.

I want to build a life where love, work, friendship, adventure, family, purpose and joy all get a seat at the table.

So this holiday weekend, I’m taking a little of my own advice.

I’m celebrating one year of The Love Story Lab.

I’m celebrating six months of this wonderful Substack community.

I’m celebrating every client who’s trusted me with a chapter of their story.

Every colleague who sent a referral.

Every conversation that challenged me to think differently.

Thank you for trusting me with your stories.

Here’s to the surprise and delight in the chapters that are still ahead.

Welcome to Dear Kara, a weekly column where I address your dating dilemmas, communication challenges and relationship quandaries with honesty, nuance and practical tools you can actually use.

All identifying details have been changed.

If you’d like to submit a question, click the button below. If I select your question, I will send you a personal email with the response (in other words, you don’t need to be a Substack subscriber to submit, so don’t be shy.)

Ask Kara Here

On to this week’s submission!

Dear Kara…

I’ve been dating someone for a couple of months, and things are going really well. We haven’t talked much about our past relationships, though.

Part of me is curious. I want to know what his last relationship was like, what he learned from it and why it ended.

But another part of me worries that bringing it up will make me sound like I’m trying to define the relationship or move things too fast. I don’t want him to think I’m interrogating him or comparing myself to his exes. Basically, I don’t want him to have to fumble through a conversation he’s not ready for and end up sprinting from the dinner table. For good.

And honestly, I’m not sure I want to answer all of those questions about myself yet either.

At some point we need to have these conversations...right? I am curious...

- Curious but Cautious

Dear Curious,

Whether you’re curious about someone’s family, their last relationship, the kind of music they like or what they had for breakfast, consider this a good sign. It means you’re genuinely interested in getting to know the person you’re seeing and discovering whether the two of you are compatible.

You’ve likely cleared the attraction and chemistry hurdles, and you’re now making your way around the compatibility track. The commitment finish line is still somewhere ahead.

Which is a wonderful place to be.

Sometimes I wonder when we started treating conversations about past relationships as if they’re dangerous territory. Like you, my clients worry that asking means they’re trying to define the relationship, move too fast or compare themselves to someone’s ex.

But I don’t see it that way.

If you’ve been following along at The Love Story Lab, you know I think of relationship history as an important part of someone’s Love Manual.

Our past relationships are often where we learn how we handle conflict, show and receive love, recover from disappointment and discover what we want in a partner.

The details of past relationships - friendships, romantic relationships, situationships and everything in between - offer clues about the person sitting across from you today.

When having the relationship history conversation, the goal isn’t to get the dirt, uncover a red flag, unpack baggage or even understand what the ex was like.

The goal is to understand who those relationships helped the person you’re dating become.

Which is why curiosity is such a good thing.

You’re not asking because you’re trying to decide whether they’re in or out. You’re asking because you’re eager to understand their story and, ultimately, them as a person.

When two people are genuinely curious about each other and begin to share their lives, intimacy tends to grow naturally.

So to answer your question, it’s less about when to start asking about past relationships and more about how to ask about someone’s relationship history without making it feel like an interrogation or some kind of relationship milestone.

Here are a few of my favorite questions, along with a mindset shift that makes these conversations feel less like the third-degree and more like two people getting to know each other.

Read more

The best dates happen between two people who are both interested and interesting.

Being interested means showing up with curiosity. Asking questions. Listening. Asking follow-up questions because you genuinely want to know the other person.

Being interesting is different.

It isn’t about climbing Mount Kilimanjaro, speaking four languages or always having the funniest story in the room.

Being interesting is about being engaged in your own life.

Trying things.

Collecting stories and generously sharing them.

Being willing to surprise yourself, and laugh at yourself every once in a while.

When you’re engaged in your own life, you become someone who’s easier to connect with. Curiosity is magnetic. Participation is attractive. Your willingness to engage with the world gives you stories to tell, confidence to borrow from and ultimately, makes dating so much more fun.

This summer, I’d love to offer you a challenge.

Instead of asking, What if I meet someone?

Ask...

What if this was the Summer of What Ifs?

A summer where every small yes makes your life a little bit bigger.

Not every experiment will lead to romance, and not every idea will become your new favorite hobby. But every time you choose curiosity over routine, your world will expand.

And who knows what, or who, might become part of it.

What If You Started With You?

Before we talk about dating apps or meeting people, let’s start with the person you’ll spend every single day with this summer: You.

What if...

...every time you left the house, you paused for five seconds and thought:

“Today might be the day I meet someone who changes my life. I’m open to that happening. Universe, do your thing.”

Not because you expect it or because you’re putting pressure on every interaction.

But simply because you’re open to the possibility.

What if...

...before checking your reflection one last time, you gave yourself one genuine compliment instead?

Maybe it’s, Okay, Kara. I see you in that tank top.

Maybe it’s, Good on me for swiping for thirty minutes. Time to go have some fun.

Maybe it’s simply, I’m proud of you for sleeping in today. You must have needed the rest.

What if...

...you wore something you’d usually never dream of wearing?

A bold print.

A flowing caftan.

Bright kicks.

The giant floppy hat you’ve convinced yourself is “too much.”

Don’t be surprised when you draw a few Love your shoes… or Nice hat!s. Keep the good vibes going with genuine thanks and offer a compliment back.

What if...

...you ran, walked or biked a completely different route with one goal: finding a coffee shop you’ve never visited?

Maybe you discover your new favorite neighborhood. Maybe you meet someone new. Or maybe nothing remarkable happens except that you remember there’s still so much left to explore.

What if...

...you made yourself a Summer Treat List?

This is the opposite of a to-do list. It’s a Guess What I’ve Done! list.

Write down ten things you’ve always wanted to experience simply because they sound fun.

Drive a golf cart.

Play croquet.

Watch the sunrise.

Read in a hammock.

Take a walk before work.

Make a mocktail.

Rent a kayak.

Dance barefoot in the grass.

Watch an outdoor movie.

Learn to juggle.

Whatever belongs on your list.

Then actually do them.

Now, What If You Changed the Way You Use the Apps?

What if this summer you experimented with a different approach?

What if...

...you only spent thirty minutes on the apps three times each week?

During those thirty minutes, message everyone you’d genuinely like to meet. No overthinking. No waiting three days. No wondering who should message first.

Just send it.

When the timer ends, close the app and go live your life.

Then here’s the experiment.

What if you let that be enough?

What if success wasn’t measured by matches, replies or dates?

What if success was simply:

I showed up.

I initiated.

I stayed open.

Those are wins completely within your control.

And What If You Became More Open to Serendipity?

Here’s where things really get interesting.

You’re not trying to meet your future partner every time you leave the house. You’re becoming someone who participates, so when that future partner does show up, you’ll be ready.

What if…

…you complimented one stranger every time you left the house?

Picture yourself waiting in line for your morning coffee.

“Flawless fade.”

You’re reaching for peaches at the farmer’s market.

“That color looks incredible on you.”

You’re checking out at Target.

“Your nails. YES.”

Maybe that’s the entire interaction. Maybe it turns into a conversation. Either way, you’ve probably made someone’s day a little brighter.

Including your own.

And now you’ve got a story to tell on your next date.

What if…

…you talked to five new people at every wedding you attended this summer?

You’re waiting in line for the bar. Instead of reaching for your phone, you turn to the person next to you.

“So...how do you know the couple?”

A few minutes later you’re waiting for the restroom.

Another opportunity.

You’re grabbing dinner from the buffet.

Another opportunity.

You’re catching your breath after dancing to your favorite song.

Another opportunity.

Before the night is over, you’ve had five conversations with people who were strangers when you walked in.

Will one of them become your spouse? Who knows. But one might become a friend. One might introduce you to someone. Or one might simply remind you that talking to new people is a skill that gets easier every time you practice it.

That’s a win that expands your world and makes telling an interesting story on your next first date just a little easier.

What if…

…you gave yourself one wildcard experience every week?

Just like I advocate for giving yourself a human wildcard when swiping, the same holds true for experiences.

Say yes to the invitation you normally wouldn’t.

Take the dance class.

Go to trivia.

Attend the outdoor concert.

Browse the neighborhood festival.

Visit the town you’ve always meant to explore.

One wildcard every week equals a whole collection of stories you’ll carry long after summer ends.

What If Every Date Included One Tiny Adventure?

Become more interesting by creating interest on the date itself.

Instead of another drink at another bar...

Play mini golf.

Visit a botanical garden.

Walk through a street festival.

Rent a paddle boat (preferably one shaped like a swan).

Take a sunset walk.

Find the best taco truck in town.

Or tell your date you’re having a Summer of What Ifs and ask:

“What’s one thing you’ve always wanted to try this summer?”

The question alone is interesting.

None of these What Ifs guarantee you’ll meet your person this summer.

I’d argue they do something even better.

They make you someone who’s getting the most out of your own life.

Which leads to...

Better stories.

Better conversations.

Better first dates.

Better relationships.

Better summers.

So here’s my challenge.

Choose a handful of What ifs… from this list.

Or write ten completely different What Ifs of your own.

Then commit to the list.

Do it for the plot.

Do it because life is more fun when you participate in it.

Do it because becoming more interesting has a funny way of making dating more interesting.

And who knows?

Maybe this is the summer you meet someone who changes your life.

Or maybe this is the summer you change it yourself.

Either way, sounds like an interesting summer of love to me.

Welcome to Dear Kara, a weekly column where I address your dating dilemmas, communication challenges and relationship quandaries with honesty, nuance and practical tools you can actually use.

All identifying details have been changed.

If you’d like to submit a question, click the button below. If I select your question, I will send you a personal email with the response (in other words, you don’t need to be a Substack subscriber to submit, so don’t be shy.)

Ask Kara Here

On to this week’s submission!

Dear Kara…

I’ve started dating again after a long relationship, and I’m already dreading one question: “What happened in your last relationship?”

I don’t want to spend a first date talking about my ex. At the same time, I don’t want to seem evasive or like I have something to hide.

How do I get out of conversations I’m just not ready to have without making things awkward?

— Ready to Move On

Dear Moving On,

You’re making me think of the holy trinity of old-school dating advice: Don’t talk about politics, religion or exes on a first date.

But in this case, you’re not the one bringing up the ex chat - you’re trying to navigate what to do when someone else gets the past relationship party started on an early date.

This might be a hot take, but I don’t think any topic is automatically off-limits on a first date.

Religion? A conversation could reveal your deeper values.

Politics? It might be a lens through which you view society and the world.

An ex? Most daters have one or two in the Relationship History chapter of their Love Manual.

The topic itself isn’t usually the problem.

It’s how we talk about it.

The best first dates aren’t devoid of meaningful conversations. They’re built by two people who approach those conversations with curiosity, self-awareness, respect and a genuine desire for connection instead of fact-finding, box-checking, judgment or avoiding certain topics altogether.

I’ve found that most people spend more time deciding what they’re going to wear vs. what they’re willing to share on a first date.

While I’ll never advocate for laying your relationship dirty laundry out on the dating table on night one, I do think there’s a way to acknowledge your past and signal that you’re genuinely excited about your future.

This is where a little forethought goes a long way before hopping in the Uber on your way to drinks…

Read more