Is Sleeping With Your Ex Always Such a Bad Idea?

But sex as exes was entirely different. (He made non-accidental contact with my clit.) Thanks to the meager amount of confidence I’d scraped together since our breakup, I had just enough perspective to see him—and our terrifying relationship—more objectively. It wasn’t as simple as a mid-fuck epiphany, but I felt more in control, more like a version of myself that I liked. It was sleeping with my ex that provided me the clarity to truly, actually, no for real this time, finally get over him.

And yet, there was a still part of me that hated that I had to fuck him to get there. I wished I’d found a better way to move on, like hot yoga, or joining a cult, or becoming more Instagram famous than him. Isn’t that what people do? So I find myself back at the same question: Should you sleep with your ex?

“Of course you should,” declared my friend Malcolm. Malcolm is a problematically charming literary editor in his 50s. He’s also my greatest enabler—it’s with him that I smoke, have the third martini, and send that 2 a.m. nude I’ll later regret. “It’s such a shame not to do something simply because you think it ‘won’t be good for you,’” he urged. “It’s better to take the risk of it being great.”

“So have you actually slept with an ex?” I asked.

“Loads,” he said. “Look, there is no rule—whether you should or shouldn’t is just a trite question for a sex column—no offense. Sure, maybe it will turn out poorly, but then you’ve learnt something about yourself. You become a better, stronger person by putting yourself in danger. And if it doesn’t feel good, you can just stop. It’s all part of the process.” He shrugged. “But maybe I’m just playing devil’s advocate.”

While I share Malcolm’s aversion to relationship “rules”—you know, wait three days to text him, no anal after Labor Day, et cetera—I do feel like having some boundaries in order to protect yourself from mental collapse isn’t such a bad idea. Because the reality is, sex with an ex is never uncomplicated. And though it may seem more appealing than railing your way through an infantry of drunk randoms, you can’t go in blind.