This week’s episode of And Just Like That—the Sex and the City reboot that has trauma-bonded us all—saw the romantic return of Carrie’s ex, Aidan Shaw. Watching the show, I often find myself wondering what Samantha Jones, whose absence is palpable, would think about what her flailing friends are up to. My hunch is that she wouldn’t approve of Carrie double-dipping. As Samantha put it in Season 4 of SATC: “Sex with an ex can be depressing. If it’s good you can’t get it anymore. If it’s bad you just had sex with an ex.”
Popular theory has it that banging your ex opens up old wounds and cock-blocks you from moving on. Okay, sure. Personally, I’ve rarely had the willpower to follow this guideline. 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. In this way, I’m a Miranda: I can’t help eating the cake out of the garbage. And yet, watching sparks fly between Carrie and Aidan two decades post-breakup, I couldn’t help but wonder... is sleeping with an ex always such a bad idea?
In my late 20s, I ended a nearly three-year relationship that was deeply unbalanced. Basically, I’d been sexually obsessed with the guy for years via the Internet, then real-life 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.)
One issue was that he wasn’t particularly interested in having sex with me. I spent many a tragic night stealthily masturbating next to his snoring body. (We’ve all been there?) 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-20s “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’d mostly moved on, but part of me still wanted to prove to both of us that he’d been wrong to reject me. Long story short, coffee turned into banging. 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 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.
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 want to pull your ex into your masochistic depression spiral, so they can’t move on either? Maybe. Is it because you’re secretly trying to get back with them? This, I’d argue, is dangerous. And yet so many of us have been there: You go back to an ex insisting “It will be different this time!” You’re in the honeymoon phase again, you’re multiple orgasms deep before noon, and then the cracks begin to reappear. Because while your renewed infatuation might give you temporary amnesia, your issues remain: He still donates to Ben Shapiro’s Patreon, and you still hate his dog. Or whatever.
But maybe you get a pass if, like Carrie and Aidan, your time apart spans decades, marriages, a literal plague, and “exit-out-of-grief-sex” with New York’s most forgettable man. Ultimately, when it comes to sleeping with your ex, the question isn’t Should I or shouldn’t I? but rather, What do I hope to get out of it?—whether it’s an orgasm, closure, clarity, connection, or simply to blow up your life in order to start fresh. As Carrie recently put it: “Some relationships are meant to stay in the past. And some aren’t.” True. And yet, perhaps she’s just another enabler.
