Is Sleeping With Your Ex Always Such a Bad Idea?

Popular theory has it that banging your ex opens up old wounds and prevents you from moving on. OK, sure, fine. But speaking as someone who’s never not fucked an ex, the fact that anyone has the willpower to avoid it truly baffles me. I prefer to drag breakups out for weeks, months, years if I have to—to pick the scab over and over, until it leaves a scar. This is why I identify as a Miranda: I can’t help eating the cake out of the garbage.

But unlike eating trash cake, I'm actually not convinced that sleeping with your ex is always such a bad idea.

When I was 27, I ended a two-plus year relationship that was deeply unbalanced. Basically, I’d been sexually obsessed with him for years via the internet, then IRL stalked him until he ambivalently agreed to be my boyfriend (the first time we had sex was after I waited outside his apartment, uninvited, for hours; thankfully I’m a woman, otherwise I’d probably be in jail).

Our primary issue was that he wasn’t very interested in having sex with me. I spent many sad nights stealthily masturbating next to his snoring body. (We’ve all been there.) (...Right?) He went down on me a grand total of 2.5 times, so around once a calendar year. When I first told him “I love you,” he silently nodded in response. It was pretty much your classic, mid-twenties, ‘what the fuck are you doing in that relationship?’ situation.

A year after we broke up, he invited me for a drink, to “catch up.” By that point I had mostly moved on, but some part of me still wanted to prove to both us that he’d been wrong to reject me. Long story short, coffee turned into fucking. But to be honest, I didn't feel particularly horny for him—I just wanted him to want me. Healthy!

But sex as exes was entirely different. (He made non-accidental contact with my clit.) Thanks to the small amount of confidence I’d managed to scrape together since our breakup, I had just enough perspective to see him—and our relationship—more objectively. I suddenly realized: ‘Wait... have we just been hating ourselves at each other for the past three years?’ It wasn’t as simple as a mid-fuck epiphany, but I felt a little more in control, more like a version of myself that I liked. Sure, I still slept over, but sleeping with my ex also allowed me to finally, truly get over him.

And yet, there was a still part of me that hated that I had to fuck him in order 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?

And so I find myself back at the same old question: Should you ever sleep with your ex?

“Of course you should,” declared my friend Malcolm, over lunch in downtown LA. Malcolm is a 50-something literary editor who thinks he knows everything about everything. “It's such a shame not to do something simply because you think it ‘won’t be good for you.’ It's better to take the risk of it being great.”

“So have you ever 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, etcetera—I do feel like having some boundaries in order to protect yourself from mental breakdown isn’t such a bad idea. Because the reality is, fucking an ex is never going to be uncomplicated. And though, at times, it may seem more appealing than railing your way through an infantry of drunk randoms, you can’t go in blind.

At the very least, you should be honest with yourself about your motivations. Are you sleeping with your ex because you broke up amicably, are both happy, and think sex would be a fun way to reconnect? Lol, no. Is it because you’re lonely and stuck, and want to pull your ex into your masochistic depression spiral, so that they can’t move on either? Maybe. Is it because you’re secretly trying to get back with them? This, I would argue, is dangerous. Because while your rebooted infatuation might give you temporary amnesia, your issues remain: he still donates to Ben Shapiro’s Patreon, and you still hate dogs. Or whatever.

I started thinking about this quandary again following a recent convo with my friend Sabrina, who has the most insane ex-relapse story I’ve ever heard.

Sabrina is a 30-year-old talent agent. She met Vince in undergrad, when he staggered into her dorm while her friends were pregaming for a frat party—the start of a true American romance. Sabrina told me, “The next day he Facebooked me with a line I’m sure he used on a million women: ‘How about we get married, have three kids, argue about your taste in furniture, I crash the car in a fit of rage, then we fight over whether to get a divorce.” She was hooked.

For the next seven years they carried on a tumultuous, on-again-off-again relationship. Sabrina became a workaholic Hollywood agent, and Vince became a sort-of-DJ-slash-full-time party person. It seemed their lives were headed in different directions, and Sabrina sensed it was high time kick the habit and find some stability.

But it turns out that stability is kind of a boner killer. “I kept going on dates with guys who were down for real commitment, but who I frankly found boring. I was like, I can not go on another date with a doctor and pretend to care about his passion for hiking.”

After more than a year of sobriety, Sabrina caved, and agreed to go with Vince to a Burning Man-esque music festival. “It was the best weekend of my life,” she recalled. “I let loose and unplugged from work for the first time in years. And I had the best sex of my life in a tent, on a blow-up mattress.” (I hope there were drugs involved, otherwise that’s the least relatable sentence I’ve ever heard.) While there, Sabrina discovered that Vince had become involved in the non-monogamous community. “He told me he had a cuckold fantasy, and begged me to go on dates with other guys, and send videos of us fucking.” After a brief WTF?, Sabrina decided to try it, and was weirded out to discover that she actually found it hot.

From there, things escalated. Sabrina's ex took her to her first-ever sex party, where they fucked in front of horny high strangers—and she loved it. For a moment, Sabrina felt like maybe her new, slutty self could actually make a non-traditional relationship work with her sex crazed ex. But then things got a little too crazy: “He told me for his 30th birthday he was planning an erotic soiree at a beachside villa, with themed ‘playrooms,’ erotic yoga, Instagram models, and catered vegan cuisine.” Unsurprisingly, the thought of Vince banging a harem of “influencers” in a Flashdance-themed sex cave while eating tempeh made her want to actually vomit. “It was that moment when I finally realized his wild lifestyle would always be an issue for me, and that I needed to move on. I really do love him, but we want different things.”

But ultimately, Sabrina said, she’s grateful for sleeping with her ex. “It was truly a sexual awakening for me, and I learned so much about myself. Like, my vagina was in fucking hibernation. And now winter’s over.”

Ultimately, when it comes to fucking your ex, the question isn’t “should you or shouldn’t you,” but rather: What do you hope to get out of it? The likeliest way to get what you want is to identify what it is you're looking for, whether it's an orgasm, closure, comfort, clarity, catharsis, or simply a way to rule out vegan orgies going forward. Of course, sometimes fucking your ex is simply a way to make a mess out of your life—to blow it all up in order to start fresh. But hey, if it works, maybe we shouldn’t beat ourselves up about it.