Portraits

A Fair Amount of Failures

Jo Rosenthal — Mon, 10 Aug 2026 19:45:31 GMT

In the opening pages of Congratulations, Who Are You Again?, Harrison Scott Key wrote, “I have changed a few names in this book and made efforts to downplay the physical hideousness of my enemies, where possible.”

I’ve followed his lead: names have been altered, and I’ve tried to extend the same generosity. I’d like to tell you about some of the men I’ve dated.

J.E.
Summer 2015. I got a text at 10:23 am on June 17th that read, “I’m so sorry you haven’t heard from me in a few days. I just got out of jail for a graffiti charge. It was stupid of them to arrest me. I only climbed up 15 floors and out of an abandoned apartment window just to write my name. No one got hurt… except for the cop who said he was disgusted that he had to see my crotch. My pants fell down because I had to give him my belt when they booked me. I’m dealing with some extreme gas right now, but maybe in a few days you can come over and watch me draw? Let me know…”

S.G.
His sister gave me a jar of beef tallow, saying it would be good for my skin, but I got a horrible rash that lasted for weeks. It turned out he was dating two women at once, me and some other bitch. She got to see the city, while I only saw the inside of his bedroom. Mattress on the floor, Bible on the coffee table, only dried pasta and orange juice in the fridge. One towel, no soap in the bathroom, toothbrush whittled down to the last bristles from his anxiety. He lived in a walk-up on the west side, four flights up, with a view of the Hudson if you squinted hard enough. I wonder if the other girl also stole a pair of his boxers and wore them as if they were some kind of trophy.

K.M.
On a “break” with his girlfriend, whom he was actually cheating on. He said he loved watching me write. There’s something to be said for persistence - he wouldn’t leave me alone. When I gave him a chance, he said he was busy with work, but he was actually hooking up with someone I would eventually become really close friends with. The funny thing about 2021 is that my friend and I have the exact same image in our camera rolls: separate photos of each of us lying in his bed, taken the exact same week. I’d wish him unwell, but I don’t wish him anything at all. He got in trouble at work for being creepy to too many young women. Consequences find you when you’re an ugly guy with a unibrow and a bad personality from New Jersey.

J.V.
I told him I wanted to do something grand for our first date, or I wouldn’t go on a date with him at all. He suggested we drive to the middle of North Carolina to see the eclipse. He wore tighty-whitey’s and had teeth that looked like Chiclets. He was in a band, but he said he barely knew how to play any instruments and only knew how to press buttons on a synth. I told him I didn’t think he was a real musician because he didn’t write music or lyrics, only ‘composed’ it - whatever that means. I was mean because I wanted him to get away from me. I know three other women he’s kissed, and we all look the same. He’s bald now, and his teeth look like fresh corn kernels instead of Chiclets.

B.C.
I walked into a party, and the most beautiful woman there approached me. “I’VE ALWAYS WANTED TO MEET YOU, BUT I’VE BEEN SCARED BECAUSE I’M WORRIED YOU WON’T LIKE ME.” She had dated my first long-term boyfriend after I did, and she was worried that even saying his name would trigger me. She made me guess who it was, and I couldn’t remember at first. She said he loves to tell anyone who will listen how much he hates me. He tells people I gave him cancer, as though it’s physically possible. As I sipped a rum and Coke, the beautiful woman told me she was much happier after dumping him because he used to yell at her all the time — and when he wasn’t yelling, he was crying. Then she said, “We have to be best friends because we’ve essentially shared saliva!”

M.M.
He worked at a surf shop in the mall and had a tattoo of an infinity sign on his wrist. He loved playing acoustic guitar, and I tried not to laugh as he played an extended version of “Iris” by the Goo Goo Dolls for me, tears streaming down his face as he sang.

J.W.
We went out to dinner, and when we came back, his bedroom door was locked, and his roommate was having a big house party. His roommate said that two people in his room were “doing it in his bed,” and he wanted the guy to get lucky, so he just let them and didn’t think it was a problem. My date said we should wait outside until they were finished because he didn’t want to ‘ruin the moment,’ and that after they were done, he wanted to set up his projector so we could watch some animated movies that his dad made.

J.D.
The first and only time we hung out, he told me the only reason he asked me to hang out was because I was the only girl who wasn’t busy on Christmas. He was the hairiest person with the biggest receding hairline. I didn’t know it was possible to have both. I knew it was a bad sign when my cat peed on his pants, but the joke was on him because he had to wear them home that way. He told me he tried to soak them but had to throw them away, and Venmo requested more than the amount of the pants because he said being with me cost him more than he gained.

G.C.
My high school boyfriend. He now has two kids with two different women. He messaged me a few years ago to ask if I’d ever be interested in being a stepmom. He said that although he was still with his second wife, if I said the word, he’d leave it all behind, bring the kids with him to New York, and start a new life with me. One of his kids is named Gator.

J.W.L
He called me ‘old lady’ because I was 27 and he was 25. The age difference eventually disgusted him. He told me it’s okay that he slept with all of his female friends because it’s the only way to actually know who is a real friend. He’d leave letters in my mailbox about how fate would someday bring us back together. He told me he didn’t really learn how to read until high school because it wasn’t that important if he was going to be a touring musician. All of his bottom teeth were rotten, but he said it was okay because all rockstars have that problem.

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More anecdotes to come…

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Jo Rosenthal — Wed, 24 Apr 2024 12:20:59 GMT

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Jo Rosenthal — Mon, 13 Nov 2023 04:47:21 GMT

This piece was written for and read aloud at Confessions: a series by Cassidy Grady, which can be seen every other week at Sovereign House in New York. Pieces are based on confessions anonymously written in a telephone booth at the theater.

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Jo Rosenthal — Sat, 19 Aug 2023 01:14:30 GMT

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