So far, your breakup conversation is going great. You’ve managed to avoid clichés like “It’s not you, it’s me” and “I love you, I’m just not in love with you.”
Nobody has cried yet, and you’re thinking you just might make it out of here without her bringing up the Xbox she just bought you, which you would very much like to keep. What now?
Breaking up is hard to do, but wrapping up a breakup is even harder. One ex-boyfriend, at a loss for how to end our breakup summit, stood up and said, “Be well.”
I once panicked and filled the breakup silence with “Are we good?” after saying my piece—we were not good. On one hand, what you say now doesn’t really matter:
You’ve already quit, so they can’t fire you. On the other hand, it’s usually in these final moments, when you’ve already delivered the speech you’ve been rehearsing in front of the mirror for a few days, that a reckless grenade slips out, causing a mature, adult conversation to spiral into a bilious back-and-forth.
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Here are five of those grenades, to be avoided at all costs:
“Will you be okay?”
Even if she won’t be okay—even if a day after your breakup she’ll get a dramatic haircut that she immediately hates and she’ll spend the next three to six weeks watching Law & Order, swaddled in her weighted blanket—she probably wants you to think she’ll be okay. “Will you be okay?” sounds a little self-aggrandizing. What she hears is, “How will you survive without the divine blessing of my presence? If you want to sound concerned without sounding condescending, say: “If you need to talk, I’m around.”
“You’re going to find someone so much better for you.”
The last thing I want to think about when I’m being dumped is the fact that I’m about to be single again. Unless you are prepared to offer up the names and contact information of several viable rebounds I might consider, keep the “so many fish in the sea” wisdom to yourself. Right after you’re done talking, I’m going to go kvetch about all your flaws to my friends. When they say I’ll meet someone better, I’ll be touched and soothed. When you say it, I’ll burst into tears and then spend the next few hours wondering whether you’ve already met someone else.
“I hope we can still be friends.”
Every time a man says “I hope we can still be friends,” a dolphin gets tangled in some fishing line and dies. “It’s the worst because there’s no closure,” one friend said. Besides which, when the dumper tries to initiate a friendship, it sounds like he wants to have his cake and eat it too—that he wants to date other people while still enjoying the dumpee’s good qualities. If you’re ever going to be friends, it’s up the dumped party to initiate it.
Where “I hope we can still be friends” doesn’t quite provide enough closure, “good luck” is like a closure bomb. “Good luck” and its many cold variations suggests that you, the dumper, are totally cutting me loose, kicking me out of the sex nest, etc. In theory, I want to be cut loose—I want space to move on—but I also want to know that you’ll be feverishly keeping up with my personal and professional successes for years to come. If you want the dumpee to know you wish them well and will continue to care about them, say: “If you feel like it, give me an update on [specific personal or professional thing they’re stressed about.] I’m still rooting for you.”
“I’m sorry you’re upset.”
Even if you’re not actually upset about a breakup, you should mirror the response of the person you’re dumping: If they’re devastated, you should try your best to look devastated too. There’s nothing more humiliating that losing it during a breakup while the person doing the dumping stares at you, dry-eyed and stony-faced, and says, “I’m sorry you’re upset.”