This was around 2022, shortly after I’d broken up with my girlfriend, and I wasn’t taking it particularly well.
One Thursday night, I went out with some friends to Macau Trading Co. in TriBeCa. I was feeling pretty down on my luck, and my solution was to flirt with basically every woman in the place.
I was throwing out pickup lines, starting conversations, shooting my shot wherever there appeared to be a shot to shoot. You won’t be surprised to learn that nothing was working.
After a few hours of this, I decided the problem wasn’t my drunk, 25-year-old ass, but the choice of venue. The Roxy Hotel was nearby, so sometime after midnight I announced to my friends that I was going over there on a sort of reconnaissance mission. Maybe the hotel bar would be busier. Maybe there’d be some new people. At the very least, I could stop embarrassing myself in front of the same group of women.
As I was walking into the Roxy, I opened the door for a woman who happened to be entering at the same time.
She was very attractive and definitely older than me, maybe in her late thirties or early forties. We started talking, and I told her I was looking for the bar.
“Oh, so am I,” she said.
Perfect.
We went looking together, but the Roxy was surprisingly dead. It was probably 12:30 by then. We checked the hotel bar, then went downstairs, where there was some kind of cabaret space, but whatever had been happening there was already over.
“I’m actually with some friends at Macau,” I told her. “Want to come?”
She said sure.
So after spending the entire evening unsuccessfully trying to pick up women, I returned to Macau twenty minutes later with one.
Let’s call her Claire.
I introduced her to my friends, got her a glass of wine, and we started flirting. People gradually began peeling off because it was a Thursday and they had work the next morning. Eventually there were only three of us left: Claire, my friend Nicole, and me.
After a couple of rounds, Claire said she was going back to her room at the Roxy and mentioned that she was going to do shrooms. I let her know that I fucking love shrooms, which resulted in a fairly reflexive invitation to join her.
Nicole decided to come too, which wasn’t exactly what I was hoping for. I’d spent the entire evening talking to anyone and everyone in the name of getting lucky, so I thought my intentions were pretty obvious.
But Nicole wasn’t reading the room, and I couldn’t figure out a way to let her know that, against all odds, I appeared to be on the cusp of not striking out.
Back in Claire’s room, she pulled out an assortment of drugs and powders. She changed clothes and asked me to unzip her dress, so things were clearly moving in a direction I was very psyched about. The only problem was that Nicole was still sitting there hanging out with us. Then Claire started telling us about her life.
She worked in a creative field and had done some writing. She was published. Pretty famous, even. But there was another part of her life that I hadn’t seen coming at all: she’d spent years as a high-end escort.
She told us stories about wealthy clients, extravagant trips, and the kind of people she’d met through the job. At first I wasn’t completely sure how much of it to believe.
So at some point I went to the bathroom and Googled her.
Holy shit!
Everything she described checked out. This woman I’d randomly met walking into a hotel really had spent years making serious money as an escort.
I’d been attracted to her from the moment I saw her, but once I knew her backstory, I really wanted to fuck her. Partly because the whole situation had become so improbable, and partly because I knew that if I actually pulled it off, this was going to be a fantastic story.
Suddenly I felt like I had to get it done. I just wasn’t going to pay for it.
I’d never paid for sex before. I wasn’t morally opposed to sex work, but it wasn’t something I’d ever done. Plus, knowing that plenty of other guys had paid Claire serious money made getting her to sleep with me for free start to feel like a game.
Meanwhile, because we were on mushrooms and apparently the night wasn’t weird enough already, I had somehow started pitching myself as her business manager.
She was telling me about some creative projects she wanted to pursue, and I was basically like, I can help you with this. I can manage you. We exchanged numbers and proceeded to have what felt, at the time, like a completely legitimate conversation about working together.
Eventually, likely due to this nonsensical, impromptu business meeting, Nicole left.
Now it was just Claire and me, probably around 3:30 or four in the morning, both on shrooms and both horny. Sex seemed imminent. The only thing left to establish was whether she expected money to change hands. She absolutely did.
I told her I wasn’t paying, and we basically started negotiating. Here was a woman who was accustomed to men paying large sums of money to sleep with her, and here I was trying to convince her that tonight she should make an exception.
My strategy was this weird, drug-addled mashup of flirting, bargaining, making my case, and making it clear that I was willing to leave.
I told her I had a big dick one minute; I threatened to leave the next.
I think I may have even said, “I’ll walk out of here right now!”
Eventually, inexplicably, she acquiesced. This one was on the house.
We had sex. I used a condom. The whole thing was surreal, but mostly I remember this ridiculous sense of accomplishment that I’d somehow pulled it off without paying.
By about 4:30, I was done. I had work the next day, so I got dressed and left the Roxy thinking, what the fuck just happened? A few hours earlier, I couldn’t get anywhere with anyone. Now I was walking home after doing shrooms and having sex with a former high-end escort I’d randomly met at a hotel.
We actually texted for a few weeks about some of her projects before we each seemed to decide that the whole thing was getting too weird and let it fade away.
So I never became her manager. I never paid her either. So I guess I came out ahead?
