How Many Times Can You Hookup With An Old Fling?

Photographed by Brayden Olson.
Casual sex is supposed to be fun and easy, but when you start having sex with a friend with benefits it might not feel so simple. Everyone from your friends to random websites will list the "rules" you're supposed to follow — no cuddling, no sleepovers, and no texting unless you're sending a booty call. All of the hubbub around rules is meant to keep both you and your sex buddy from catching feelings, which is apparently the death knell to any casual relationship.
But the rules you set the first time around might be even more important when you revisit a fwb after some time apart. After all, circling back to the same person (even if it's just for casual sex) has to indicate that you care about them, right? At least, that's what many people might think. And starting to care for someone leads you into tricky waters. So what's the deal? Is it always a bad idea to ask an old fwb if they'd be down to start sleeping together again? Are you only allowed to circle back once? Or can you revisit the relationship whenever you want?
Just like any other relationship, the "rule" about circling back to an old hookup partner isn't hard and fast. "There's no limit on how many times you can revisit a play partner," says Lia Holmgren, a relationship and intimacy coach based in New York City. What's most important is that both people are clear about what they want from the sexual partnership, with themselves and each other, and that they make sure their boundaries are clear every time they start sleeping together again. "If they're both on the same page and they're having a good time and have no expectations, why would you limit your good times?" Holmgren says.
So there's no strict number of times it's okay circle back to a fling when you're in-between relationships, but there are still times when reaching out to an old friend with benefits isn't the best idea. If it's clear that your fwb is starting to have feelings for you (because they're asking you more private questions and trying to learn about your life and what you want in a partner), then it wouldn't be kind of you to ask for casual sex. Maybe the first time you slept together several years ago you both agreed that the relationship wouldn't be anything serious, but over time your fwb has started to want more.
"So the rule should be that every time you reconnect, you have to have an initial conversation, and say, 'Hey, I really want to see you again, but just for fun. Is that okay for you?" Holmgren advises. Don't just dive back into the casual sex assuming that everything will be the same as it was before.
And if your ex-fwb does confess to having feelings for you (feelings that you don't return), then it's best to stop seeing that person altogether. "It might sound harsh, but not seeing someone is much better than breaking someone's heart," Holmgren says. If that's the case, then it might be time to find a new sex buddy.

More from Sex & Relationships

R29 Original Series