Another Jane Pratt Thing

Another Jane Pratt Thing

It Happened To Me: I Went On Vacation With A One-Night Stand And He Turned Out To Be A Psycho

PLUS Jane really wants to pay you to be part of this thing!

Dec 21, 2025
∙ Paid

Hello people!

This is just my kind of It Happened To Me: an odd circumstance that’s super specific and on a topic I’ve never seen covered, but one that also feels (to me) universal. Almost to where I thought while reading it, wait, did this happen to me too? But no, it didn’t - unless I blacked out and forgot it. (But I didn’t.)

This IHTM (pressure to send in your own to me below), encapsulates for me that odd phase of life that happens generally sometime in your 20s where you wind up in random places, with people you barely know, doing things you have never done before, and it would take too long to even try to explain how you ended up there. Sometimes there is life risk involved, but often simply awkwardness, embarrassment, humiliation or giddiness (the standard emotions of maybe not every 20-something but certainly me when I was that age).

Like I have a memory from my early 20s, just before starting Sassy, of being on a boat with some tangential acquaintances somewhere on the Mid-Atlantic coast (maybe Delaware? maybe Maryland) and that night sleeping with a guy from the boat who I think was named Michael at his apartment before I had to hurry out the next morning (where in the hell was I hurrying to? Back to my friends? Home? Which home - my mom’s? And by train or bus or car or what?).

But my 20s anecdotes are certainly not all sex-related - it's not like I slept with the whole random world during that decade, just maybe 2/3 of it. For example, there was another time where I ended up having Seder on a snowy evening in the dining room of a suburban family in New Jersey I have never seen since. I didn't know anyone, so how or why did I get there? God knows. Or the time I wound up at a historic hot-springs spa in West Virginia with a guy I didn’t like and my uncle - and my uncle’s mistress who I hadn’t known was joining. I wasn’t drunk or drugged in any of these specific scenarios, though they all have that altered-state vibe to them and though that excuse would make more sense. It was all part of that strange unmoored time when you say yes to everything (I still do but the questions are different now).

So I highly related when I received this submission this week from Kate (whose full name, Kate Messinger, was so familiar to me, and apparently it's because she used to intern at a blog that was dedicated to bashing me – small world!). I loved the funny details of it, as I said. And her willingness to tell it. And her ultimate takeaway, which I think also makes it part advice column for any of you currently in that phase of life I'm talking about.

Now bear with me just before we get to her piece while I quickly try to tell you another It Happened To Me-related story that happened (to me!) today to see if it makes sense to you or if you think it's funny, as I do:

I got a submission months ago from a great writer whose manuscript revolved around how I was her long-time idol, and it culminated with a night where she met me and I passed her the cauliflower. It is an extremely well-written piece but I've just been grappling with whether I could see publishing a story where the point of the story was her excitement at meeting me. I mean clearly I have a big ego. I had a magazine named Jane, for starters. This one just felt too overtly self-promoting for even me. So I have held onto the story trying to figure out what I could do with it or when and how I could help this writer in some other way, potentially without running that story.

Cut to this morning when my friend asks me if I saw this recently published piece about a night that we were all out for dinner. No I hadn't, so she sent me the link. Well it was a story about that same night by the same writer and I'm not going to name the celebrity she refers to because then it would be too easy to find the story and know which writer I'm talking about, but the premise of the article was how this very very famous celebrity, who was there that night also, took bites of her entree. I wasn't mentioned in the piece at all, much less did I pass any cauliflower. I now have more respect than ever for that enterprising writer, appreciate the ego deflation and hugely admire her for presenting her story in whatever way works for her to get it published. Go, freelance writer, go!

So on that maybe-decipherable note, please consider sending me an It Happened To Me story from any time in your life about anything at all you’ve experienced. I would love to pay you a whopping $50 for it and run it here accompanied by all the praise you deserve for submitting it. Send it to jane@anotherjaneprattthing.com. I love you!

Jane

PS You may know that I’m operating as a one woman show here at AJPT for right now, but you also know that Charlie valiantly jumps in to help me out making the opening images look presentable. When I found out he was sick yesterday, I told him not to make this one for today. I said I handled it myself and the version just above is what I proudly showed him. (Yes, in addition to the odd placement of text on that layout, because of my formatting issues I wasn’t even able to put my whole quote on the image, so I just started cutting words to make it fit.) Charlie took one look at my janky attempt here and mercifully sent me the one you see featured at the top. From his sick bed! Thank you always, Charlie!

PPS Tell me your strange 20-something stories or anything else in the comments so I don’t feel self-conscious about potentially boring you with mine. THANK YOU!

Sassy Ts For All Genders!

It Happened To Me: I Went On Vacation With A One-Night Stand And He Turned Out To Be A Psycho

By Kate Messinger

Back before my days of blissful baby cuddling with my husband and headaches after one glass of wine, I was a bit of a romance thrill seeker. Some may say I was in the Hannah Horvath school of thinking: put yourself in dumb situations, you might warrant sexy content for the ever-looming memoir. I often did things just for the story. But GIRLS can’t be to blame for all our regretful decisions in the 2010s, so let’s say I was acting independently when I invited a one night stand on my family vacation.

In the early days of dating apps I went on a very normal, very drunken date with a video game designer in Brooklyn that ended in me going back to his apartment. He was in a band. He was tall. He had a job. And the sex, as I remembered it, was better than average, so the possibility of seeing each other again seemed in the cards. The only thing was I was leaving for Puerto Rico in the morning for a family vacation, so it would have to wait. But it didn’t.

In between snorkeling excursions with my family and drinking Coquitos with my mom, we kept our conversations rampant on my flip phone. As I texted, weightless in a hammock in the humid breeze, the hazy outline that he was that night grew into a full grown Rom Com stud.

“When will I see you again?” he asked.

“Just come to San Juan,” I joked.

“I just bought a ticket!” he said.

Turns out he wasn’t joking.

Me at 27 in a Puerto Rico dive bar, taken by my sister before my one night stand crashed my family vacation.

I snuck away from my family to meet him on the beach the next day. This was the Mary Kate and Ashley beach rendezvous of my teen dreams! And I figured if he could afford to fly during peak season with one day’s notice, he might really be a catch for a poor twenty-something writer like me. Or at least the story would be enough.

But when I saw my one night stand I hardly recognized him compared to the vision I had created in my head. Deathly thin, hunched and coughing, skinny jeans and converse trudging through the sand. He awkwardly hugged me and said how expensive drinks were here, that his mom didn’t give him enough to cover more than the flight and hotel so we’d have to go gambling later to try to win big. His parents were concerned about him in the New York cold–he’d developed a lingering cough–and a trip sounded like a good chance to get him out of his rut of playing video games all day. “I think I have enough money to go jet skiing though…”

Right. The memory of the date came back, his vague answers were clear now. Not a video game designer by trade, more of a video gamer by hobby. Not really in a band, more just into bands. It wasn’t the first time my memory of a night had been manipulated by my own narrative, but this time I had maybe gone too far. But here we were, a second date an ocean away from home. Might as well go jet skiing.

Me in Puerto Rico in 2015, taken by “the guy” before I realized he was on the incel fast-track. Coconut was the best I ever had, though. [You all know me well enough to know that of course I asked if there was a picture of the guy, but this was the closest Kate had to that, and I was highly impressed actually that she found a picture that he had taken. Now I'll try to zoom in and see if I can see his reflection in her glasses. I like to know and see everything! You too? -Jane]

I had to get off after the first time around; he was too fast and wouldn’t stop. He spent the next 4 hours maxing out his credit card on the jet ski rides while I watched him from shore, trying to convince myself to run away back to my family.

I went to dinner with my parents while he slept and I let them know a friend was in town so I’d be going out that night. There’s something about being twenty something that gives you stamina to put up with bullshit your older self would never commit to. I had to see it through.

We went to the casino. He wore a suit and must have asked his parents for more money because he bought us drinks and gave me some chips to play with. I was up $300 on roulette, more money than my barista paycheck. This is more like it! I thought, knowing full well his family money wasn’t worth me sticking around in the long run. But at least the story was paying off.

We went back to his small hotel room and attempted to have sex.

Writers like Kate, and hopefully you, get paid for their work here because you sweet people pay just a little bit to read it. Isn’t that nice how that works? Thank you, thank you, thank you if you do.

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