Never Have I Ever: Had Sex With My Ex

Here’s Why Hooking Up With Your Ex Is Such a Bad Idea

Have you ever played “Never Have I Ever” before? Here are the rules: Everyone puts up ten fingers, and you go around in a circle and one by one share something sexy or scandalous that you’ve never done before. When someone else shares something you have done, you have to put one finger down — and of course, drink. The first person to put all 10 fingers down loses (or wins, depending on how you look at it).

Well, AskMen is still playing Never Have I Ever, and the rules are simple: In each edition of this column, we speak to someone about doing something new in bed, whether it’s a long-time fantasy, something that just happened, or even something they regret. They tell us everything so you get an inside look at what some sexual experiences are actually like.

Sex with an ex. The phrase itself is a line that invokes poetry. It even rhymes.

The return of the lover is a trope included in plays, songwriting, and, most cruelly, in real life across centuries, no, millennia. As long as people have been breaking up, they’ve also been getting back together for rushed, hasty fumbling rolls in the hay one last time. And then another one last time. And then another — you get the idea.

That’s one of the biggest problems with having sex with an ex. It’s happening in a context with no rules or guidelines, with extremely high emotional stakes. The potential for things to go wrong is extreme — probably close to 100%.

And yet, the people involved are probably — if they recently went through a breakup — emotionally vulnerable and possibly not at their best from a decision-making standpoint. In short, no matter how exciting or validating it might feel to hook up with someone after one of you rejected the other, it’s almost always a terrible idea.

Of course, I’m sure some sex-positive, caring people have great sex with an ex without negative consequences. But this particular article’s musing on sex with an ex is a tragedy, not a comedy. I spoke to a Brooklyn-based guy we’ll call Dylan about what can happen when you have sex with an ex from an unhealthy relationship and fall right back into old habits.

AskMen: You recently had sex with an ex. Would you give our readers a little bit of background?

Dylan: About a year ago, I had sex with an ex, who I got back together with, before it went up in flames, with twice the pain, and I would not advise it to anyone and never do it again.

Never say never! What happened?

I was in an on-again, off-again relationship with someone I’ll call Amy for about six months. The sex was great. We live in New York and the same neighborhood in Brooklyn; as any New Yorker knows, that’s golden. That’s better than a unicorn. You can walk to her place in less than 10 minutes. After a lot of conversations, we finally ended it. Then, like a week later, she texts me that she didn’t want to be alone. She’s dealing with depression. She wants me to come over. So I go over there, we have sex, and somehow end up getting back together.

To be fair, on her part, it sounds like she wasn’t in a place where healthy, casual sex was on the table for her. If she’s too depressed to be alone…

I know, I know, I fucked up. And for the record, since we split again, I’ve since spoken to her friends and even texted her sister that I’m worried about her and they said her therapist knows and she’s doing better. I know that I fucked up. Yes, I was drunk and horny, but here’s the thing. I really do care about her. If she’s having a hard time, even now, thinking about it, I want to be there for her. And I hope one day we can be friends, without the sex, so I can do that in a healthy type of way, you know? We were never compatible. When we first broke up, which she initiated, she stated that herself. I know.

That’s good that you know, I just…Do you think you could ever have sex with an ex again, and have it be fun, casual, and healthy?

Yeah, maybe. I’m sure it works for some people. Maybe it’s easier if you’re poly, I’m pretty vanilla and monogamous, which I guess makes me boring now. But I think it’s a recipe for disaster. I’m back on the apps and only dating new people who I know have long-term potential, are in a mentally healthy place, and that I have not dated before.

So how did you two get back together so easily?

We just fell into the same exact routine. I spent the night. I hung out with her dog. We went to brunch the next day. We hooked up again a few days later. When you break up with someone, and then start hanging out with them right away, it’s just so easy to fall into the same exact routine. We watched TV together. We weren’t hooking up with anyone else, so we just said we were monogamous. I got to delete Tinder, which I hate. I’m back on it now.

…And will you share how the breakup went down?

One night she was over, and I didn’t feel like having sex. My friends had been giving me shit for it, and I was having doubts, and not having sex seemed to be like the right thing to do. I said that we could just hang out some nights and not have sex and that would be okay. And she got mad and accused me of friendzoning her, basically, when she was officially my girlfriend. And then it all comes out and the issues start spiraling. She wants kids, I’m not ready. We go through the exact same breakup.

Wow, you really should not have had sex with this ex.

I know. I know.

Any big lessons learned or advice for our readers?

Yes. It’s hard when you care about someone, but sometimes, when you care about someone, the best thing to do is to stay away. Does that make sense?

Yes.

Hooking Up With an Ex — From Her PerspectiveThings to Stop Doing If You Want to Get Over Your Ex
How to Avoid Rebound Relationship Mistakes

Source: AskMen