both sides of a breakup

He Wanted to Be More Than Her First One-Night Stand

Illustration: Jeni Zhen

In “Both Sides of a Breakup,” the Cut talks to exes about how they got together and why they split up. Andrea, 32, and Josh, 28, met at karaoke and didn’t go on a single date, until their last. This is their story.

Andrea: The most important thing to know is that I had been with my ex, David, for 15 years. We met when I was 15. We met in high school, and until we broke up, he was the only guy I’d ever slept with. He’s the only man I ever lived with. Or loved.

We broke up when I was 30. David decided he was gay. Or, David was gay. That’s another story altogether. The takeaway is, at 30, I found myself single after dating a closeted man for 15 years. I had no fucking clue what I was doing.

Josh: I asked Andrea out after meeting her at a singles’ night at a karaoke bar near my house. I go to events with baked-in flirtation because I’m a pretty nerdy guy — I’m really awkward at meeting women in real life.

Andrea: He was tall and lanky and not confident at all — my friends and I were watching him from across the room as he bombed every time he talked to a woman. We basically ambushed him, like the dating police. We were like, You’re very cute, what is the issue here? Let us help you. We were all single and kind of curious about him. He seemed like a fun project for the night.

Josh: I really liked Andrea’s friends, but I especially liked her because she had really curly hair and I love curly hair. No, she also had a great personality. She was funny and engaging. I felt slightly less uncomfortable around her than I do with most women, so that was a good enough reason to ask for her number.

Andrea: I was like, “Ah fuck it, I’ll give him my number.” Everyone kept telling me I needed rebound sex. Josh seemed like a good prospect for that. He didn’t exactly look like a one-night-stand type of guy, but I don’t look like a one-night-stand kind of girl either. I walked away from that night knowing that he was the guy I was going to have sex with next. My second partner ever.

Josh: I’d been around the block sexually … there were girls in college and a long-term girlfriend. I really like sex. I’ve been told I’m not bad at it. I’ve read books; I mean, I’m a nerdy, studious academic type. I study things, and I pay attention. Make fun all you want, but it does pay off.

Andrea: This is how forward I was: I invited him to my place to cook for him. I’d just gotten my own apartment and the kitchen was the best part, so I told him I needed help “breaking it in.” I work in the food-publishing world so I had like 20 cookbooks to dig into, and he’s a chemist so I knew he’d like recipes. He was like, Yes, what time, where. No games. And no “game.”

I drank almost an entire bottle of wine before he came over. I was psyching myself up to have a one-night stand. I was also numbing myself to the fact that this would be the first person to touch me intimately in my entire life, besides David. It had been six months since the breakup with him, and we had zero contact at that point.

Josh: So, I don’t know how to put this tactfully. I walked into her apartment and she was … well, do you know the expression DTF? She was DTF. She was like a little drunk and basically all over me. I wasn’t turned off or anything, but I wasn’t that happy about it either because I was excited to get to know her better. I had been thinking about her all week and wondering things about her. I knew she’d been in a long-term relationship and that he turned out to be gay, but I was curious about the details there. It just — this has maybe never been said by a straight male before — disappointed me that she wanted to not talk and just have sex. In any case, that’s what she wanted. I obliged.

Andrea: It was great sex! Not just because I’d been sleeping with a gay man for 15 years (not that we had much sex after year five), but Josh has moves. He’s got a great body, a great everything. He was sexy and not nerdy, when he was naked. But we couldn’t be naked all the time … reality kicked in.

Josh: We had a mostly sexual relationship for three months, I’d say. I was her booty call! I didn’t love it but I accepted it. I liked Andrea … I wanted to date her. I asked her to have dinner a few times and to meet my friends, but she always had reasons not to. She had limits. I tried to be respectful.

Andrea: I was extremely into the sex and extremely not into being in a new relationship. It honestly had nothing to do with Josh. I wasn’t sleeping with anyone else and I wasn’t looking for someone “better.” For lack of a better term, I was using him. And soon, that started to feel bad for both of us. I felt guilty about it because he always wanted to hang out and I’d blow him off. And he felt frustrated and I think sad that we couldn’t take it to the next level.

Josh: Eventually, my two sisters sat me down for a little intervention. They were like, look, this girl won’t meet our family. She is not interested in your work life or friends. She’s just coming out of a major relationship that was extremely complicated. They weren’t hating on her at all … if anything it was the opposite. They were like, “She needs time and space to figure her life out … you cannot expect anything from her.”

I left that night with my sisters feeling really depressed. It’s hard to explain how a purely sexual relationship is anything but fantastic, but it didn’t feel fantastic to me. It felt depressing. The next day, I invited Andrea to meet me for sushi and she actually came.

Andrea: I figured it was like a good-bye dinner thing. I knew he was over it with me.

Josh: I asked her to be my girlfriend. I even jokingly said, “Will you go steady with me?”

Andrea: He wanted to make it official. I was just like, “No. Absolutely not.” Again, not about him. Getting into another relationship so soon would have been the worst decision of my life. Well, the second worst, after wasting 15 years with a man who watched gay porn and said it was by accident.

Josh: The craziest part of the story happened next. At the end of the sushi dinner, she said she wanted to fix me up with someone. I was pretty much floored by that. I said, “No thanks.”

Andrea: So, that night we all met at karaoke, there was another girl with us who I always thought would be perfect for Josh. And she was really looking to meet someone. He did not at all seem into the idea. But then …

Josh: A week later, I was like, “Okay, what’s her number.”

Andrea: I think they’ve gone out a few times! I honestly don’t know because I don’t know the girl that well and don’t want to follow up with her — I don’t want her thinking it’s weird for me at all.

Josh: We are now dating … it’s not that serious. But yes, I like her!

Andrea: I am in therapy. I’m doing yoga. A lot of cliché activities. David, I think, is dating a lot of men and kind of living it up. I’m going to freeze my eggs because I’m 32 now, and I still feel unready to date seriously. I think I have a little PTSD from the David thing. Josh got tangled up in it briefly, but I hope he at least enjoyed the sex. You know I did.

Are you and your ex interested in explaining both sides of your breakup? Email and tell us a little bit about yourself.

He Wanted to Be More Than Her First One-Night Stand