Winning the Breakup in the Age of Instagram

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Photo: Islandpaps/Splash News

“Brett was there,” I Gchatted my friend Holly after running into a man who’d broken my heart six months earlier. “We ­actually had a nice chat. He was a mess though. Like, unshowered, smelled weird, was carrying an iPad in the waistband of his pants because he had nowhere to put it.” She asked me what I’d been wearing. Lipstick and heels, I replied. I’d been waiting for my new boyfriend, who picked me up and briefly met Brett.

“Oh my God,” Holly replied. “That is the ultimate ex encounter? He’s nice but looks like a mess. You look awesome and are with a new guy. You won.” 

“Winning the breakup” may be a petty concept, but everyone who exits relationships regularly (or maybe just exited one very memorably) knows exactly what it means. The winner is the ex whose career skyrockets after the split; whose new wife is a ­supermodel; who looks better; who dates better; who has bouncier hair. It’s getting over your ex before she gets over you and leading a demonstratively successful life without her — but doing so in ways that at least look casual, just for yourself, definitely not just to rub it in her face, because you’re so over her, remember? And therein lies the Catch-22 of winning the breakup: To care about winning, you are forced to care about not caring about someone. Asked about her weekend plans, my 26-year-old friend Sam once replied, “I’m assembling a team of hotties to torture my ex on Instagram.”

Dating actively is to be in a perpetual state of breakup. (Even in a best-case scenario, you are spared the breakup only once.) I’m 30, but already I feel like I’ve surpassed my lifetime limit for breakups — starting at age 18, hooking up in the dorms, I was already cohabitating with my significant others. In the past decade and change, I’ve had multiple multiyear relationships, which among my peers is a typical track record. For a time, social theorists believed my generation’s defining romantic feature was the hookup. But as hooking up rapidly expanded into a series of miniature ­marriages — and miniature divorces made more confounding by social-media omnipresence and cell-phone butt dials — I’ve come to think millennial romances are defined not by their casual beginnings but their disastrous ends. We aren’t the hookup generation; we’re the breakup generation. Today I find myself entering each subsequent relationship already anticipating its end — but is breakup dread a sign that the relationship is doomed, or does the dread actually cause the doom?

Inevitably, no two people ever can desire a breakup exactly equally. Which means at least one person comes out of it feeling like a loser — and as any résumé-padding overachiever knows, where there are losers there are also winners.

“You’re familiar with the term success theater?” Sam asked when I brought the topic back up. The term gets tossed around the tech start-up world to describe the difference between presenting the image of a successful-sounding company and actually running one (tech reporter Jenna Wortham has used it to describe the act of showing off on social media). “I’m eightish months out of my last relationship and very concerned about winning,” Sam said. She then walked me through a timeline of the breakup, as illustrated through Instagram links. First, a period of silence. Then, a sexual war of attrition: pictures of Sam cavorting with new love interests, partying in a rooftop swimming pool, posing with a semi-nude actress at “Queen of the Night.” “Before that one I actually said, ‘Let’s make my ex-girlfriend jealous,’ ” she recalled with a sort of nostalgic pride, as though she were an aging football star fondly remembering a game-winning touchdown.

But what if the whole game is rigged? “Winning is complicated for me because I want to care less, but I also want to see the validation of me being cool and over it in his eyes,” my friend Maya explained in a Gchat. (Since caring in public is a loss, her name and some others have been changed.) “But that’s not really winning, because really I just want to see him again, but am excusing it by pretending I am merely showing up to ignore him. I guess the problem is when, instead of trying to win the breakup, you’re actually just trying to win him back.” Put another way: Does caring about “winning” the breakup mean you’ve lost?

Placed on the Kübler-Ross scale of loss and grief, “trying to win him back” might be aligned with stage one, “denial.” Whereas “trying to win the breakup” could be an expression of stage two, “anger.” (How dare you stop loving a girl who looks this good in a bikini?!) Or stage three, “bargaining.” (If I look good enough in a bikini, someone will love me.) And though neither attitude seems particularly healthy, the masquerade does have a certain “fake it till you make it” quality. In the success theater of breakup grief, “winning” is about reaching stage five, “acceptance,” before your partner does. Even if you’re going on Instagrammable dates just to spite your ex, ultimately you are still, you know, going on dates. You’re dragging yourself out of bed, brushing your hair, and putting your freakum dress on. A recent study found that 23 percent of recently broken-up college students reported “revenge motives” when sleeping with a new partner post-breakup; the worse they felt about the breakup, the more likely they were to seek sexual revenge. Although, one male friend noted, “if you’re looking to ‘win’ breakups like they’re UFC cage matches, where the person who climbs out of the cage with the least blood on them wins? Well then, you’re definitely a crazy bitch.” I have yet to punish him for saying that, but I’m sure it will involve some sort of holier-than-thou social-media vengeance. Once a petty cyber-winner, always a petty cyber-winner. “I mean, in a good breakup, everyone wins,” he concluded. “Ultimately it boils down to, ‘Did I fuck up?’ and ‘Was I better off before?’ The ultimate win on both sides is if you can be legitimately, unconditionally happy for the other person when they find love again.” At the time, I teased him for sounding like Gwyneth Paltrow, boasting about ­“conscious uncoupling.”

“I consider lots of sex winning,” said my friend Eric, age 31. “Back when I was young and crazy, I needed to have better first-rebound sex. So I would legit-stalk: asking friends of friends, keeping windows to each of their social-media accounts ­permanently open in Google Chrome. ­Checking the locations of their posts. Checking the events they RSVP-ed on Facebook and then showing up.” But the brokenhearted make terrible detectives: “I remember my ex had his Twitter account linked to his GPS, and he sent a tweet that showed up three or four blocks from his apartment, and I was like, ‘Well, looks like he already found some guy on Grindr who lives next door.’ When in reality it was probably just some GPS fluke.”

“Wait, GPS shows down to the block?” I asked in horror. The dangers of Big Data had never really hit me until I saw social media through the eyes of an ex-boyfriend scorned.

“Thank God my last breakup was with someone who had no social media,” Eric continued. “It took literally just a week to get over that guy.”

Of course, winning is subjective. Though memorializing my victory over Brett in this magazine could be a bald-faced bid for a win, the event is now so long in the past that even acknowledging that I remember it is definitely a loss. Even the best breakup victories tend to be Pyrrhic. Or, as Holly said when I described my new boyfriend’s reaction to his predecessor: “The only drawback to winning that hard is that then you want to be like, He used to be so much better!” Except, well, he wasn’t. And neither was I.

*This article appears in the December 1, 2014 issue of New York Magazine.