I’ve always believed that timing is everything. Sometimes life pulls us away from the people or things that are meant for us, and we have no choice but to let go and make room for whatever comes next. Other times, if we’re lucky, life has a funny way of bringing us back to what we thought we’d lost.
In March 2023, when COVID finally began loosening its grip and the world came alive again, I found myself at an art fundraiser in Midtown Manhattan, dressed in Chanel and sipping a martini in a room of mostly strangers. The restaurant was loud, with photographers circling the art patrons like vultures. Then I spotted my ex next to the seafood bar.
There are few things more destabilizing than seeing an ex in the wild. Thankfully, I wasn’t in sweats running around the East Village. (Timing, as I said, is everything.) He looked up, we locked eyes, and my stomach dropped immediately.
This is the problem with exes. When you meet someone new, the uncertainty is exciting. You wonder if they like you. You wonder if they’re attracted to you. You wonder if they’ll call. It’s all very thrilling and hypothetical.
People tend to fall into one of two camps when it comes to exes. There are the people who believe an ex is an ex for a reason; once it’s over, slam the door shut, delete their number, and for God’s sake, don’t go looking up their Instagram at 2 a.m. And then there are those who feel that if you loved someone once, why not give it another shot?
People break up for a thousand different reasons. Sometimes the relationship itself is wrong. Sometimes the timing is wrong. Sometimes two people love each other but are simply not capable of making it work at that particular moment in their lives. Maybe you go away to different colleges. Maybe one person moves abroad for a job. Maybe someone gets sick. Maybe you’re young and still becoming the people you will eventually be.
Sometimes circumstances change—and sometimes you change. That, to me, is the only real reason to consider going back. Don’t do it because you’re lonely, or because dating has become exhausting—and certainly not because you spent six months on the apps and are convinced that humanity is doomed. I have seen this happen more times than I can count: Someone gets dumped, proceeds to go out into the world to see what else is out there, fucks around, finds out, and then—often as winter approaches—circles back.
Sometimes people return because they genuinely miss their ex, and sometimes they return because they didn’t find anyone better. How to know the difference? For me, it comes down to what has changed between you in the meantime. Do you miss this person, or do you miss being in a relationship? Do you miss who they are now, or who they were when you were together? Have you both grown? Are the circumstances that contributed to the breakup actually different? Are you willing to forgive what happened—to not just say you’ve forgiven it, but to actually let it go? And, perhaps most critically: Are you ready to start over?
The second time around with my seafood-bar ex was very different from the first. We were older and more mature—or I’d like to believe so, anyway. And we had made a conscious decision to be together when we knew what it was like to split apart.
Ultimately, things didn’t work out between us—which, admittedly, isn’t the ending you hope for when you decide to extend an ex a second chance. But I don’t regret it.
Sometimes the point of going back is to find out what, if anything, is still there. Sometimes it’s to forgive. Sometimes it’s to see who you both became. At other times, you have to go back to the thing you lost to understand why you had to lose it in the first place.
