Author: Rob

New Yorkers can tell a lot about someone by their neighborhood. Or at least, we think we can. East Village. Bushwick. Bay Ridge. Murray Hill. Flushing. Upper East Side. Each one conjures a little persona. A type. A set of assumptions about where somebody shops, what they drink, how much money they make, what kind of apartment they live in, what music they like, and probably what they’re like in bed. Unfair? Sure. But we all do it. I’d venture to say that these geographical tells were much more pronounced in years gone by, even as recently as September 2015,…

By 2022, I was pretty tired of dating. I was 28, living in Greenpoint, Brooklyn, sharing a one-bedroom apartment with my sister, and I really did want to meet my forever person. Unfortunately, dating in New York was not producing a lot of forever-person material. The apps felt low-effort and way too casual, so after trying to find something serious for so long, I decided maybe I should stop putting so much pressure on myself and just have fun. That was when Samuel found me on Instagram. I have no idea how, but he started liking my pictures, which at…

My wife Mika and I were going through a fairly adventurous phase. Or, more accurately, Mika had decided that we should go through a fairly adventurous phase. Opening up our relationship had been her idea. Her proposition took a little getting used to, mostly because Mika was simply bound to have a much easier time meeting people than I was. She was spectacularly good-looking. Half German, half Japanese, with a gorgeous, friendly face and a million-dollar smile. She had jet-black hair, golden skin, visible abs, and an ass you could bounce a quarter off. Years earlier, she’d been a Grizzly…

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,…

I met Ricky on OKCupid, and for our first date he pulled what I considered, at the time, an extremely big-balls move. “My friend is DJing at Webster Hall,” he said. “Come meet me there. We’ll hang out onstage.” Okay. Sure. I showed up and, technically, everything Ricky had promised was true. His friend was DJing at Webster Hall. We were onstage. What Ricky had neglected to mention was that his friend had an early set and it wasn’t like the thousands of people there had come specifically to see him. But Ricky acted like his best friend was fucking…

Around 2022, I was 46, single, living in Los Angeles, and making a conscious effort to meet women in real life instead of on apps. This decision had been arrived at painfully. The problem with dating apps, particularly if you’re a creative person, is that you end up filling in blanks with what you would like to be there. Give me five pictures, a short bio, and three weeks of texting, and I’d create an entire human being who did not exist. Then I’d meet the actual person and be like, Oh. Right. You. So I was trying to use…

This was probably late 2022 or early 2023; I was around 45, living in Los Angeles, and I had mostly fallen out of love with Feeld. Feeld had started as an app for couples looking for threesomes and had evolved into a place for people whose sexual interests generally required a little more explanation. If Tinder was a bar, Feeld was the dingy, sticky-floored room in the back of that bar. More and more, that room was full of things that didn’t interest me, but occasionally I’d venture back there and see who was lurking around. That’s how I met…

It was 2022 or so. I was in my early twenties when I matched with a guy on Bumble who was probably about 25 years older than me. I would not do that now, but at the time It was something I was excited to explore. He was tall, brown hair, blue eyes, handsome. I don’t even really remember how the conversation started because it basically was never not sexual. There wasn’t any pretending that we were going to get drinks and discover we both loved hiking. It was immediately like: You’re hot. I’m attracted to you. What are you…

When I studied abroad in Barcelona, I went there with a very specific plan: I was going to meet a Spanish prince and never come home. Well, I did come home. And I got surprisingly close to meeting that Spanish prince. This was 2018-ish; I was 20, and living in a dorm with maybe 12 Americans and more than 200 students from all over Spain. The cafeteria had a rule that you weren’t allowed to sit alone, which was terrifying at first because I barely spoke Spanish. But it meant that every day I had to sit down with random…

I was 19 when I moved to Rome in January 2020. I was going to a school that has a campus in Rome, so studying abroad was almost too easy. It didn’t cost anything extra; there were about 200 of us basically living in freshman dorms again, and I could knock out my gen eds while traveling around Europe. Freshman dorms again. But make it Rome. Obviously, I had a very romantic idea of what the semester was going to be like. How can you not? I was supposed to be there for five months. I made it two. This…