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The Gentleman’s Guide to Breaking Up

Heartbreak Hotel

Persistence is generally considered a virtue. Also: knowing when to call it quits.

Today we’re talking about that second thing.

Because even with the aid of Valentine’s-enhanced romance—and the champagne, the roses, the long weekend in the woods—your last shot still came up short. It’s not that she isn’t a spectacular gal and it hasn’t been great getting to know her... but, alas, the time has come to part ways.

So take a deep breath. Prep some band-aid metaphors. There’s no sense in putting it off:

This is the Gentleman’s Guide to Breaking Up.

Be sure you’re sure. We’re not saying we don’t think you should do this—though she always seemed like a lovely girl—just that this isn’t a time for uncertainty.

So make your pro-and-con lists. Call your mother. Pull the petals off a flower. But do it all before you make any moves. By the time you go in there, know that nothing she says is going to change your mind.

Set it up. Best-case scenario: you invite her somewhere with the sole purpose of ending things. If you find yourself in a somewhat tenser, perhaps alcohol-laden situation, hold off on any final statements until the next morning.

Pick somewhere public and a little outside your usual stomping grounds. Wherever you do it will become the place you ended things—so be a gent and don’t ruin her favorite café.

Will she think it’s a little strange if you ask her to have coffee at the Starbucks by her office after work? Yes. But it’s not a bad thing if she has an inkling something’s up—no one likes to be blindsided.

No restaurants. Dinners are long. If you wait until the end, she’ll feel like a sucker for having chatted along for the past hour, and if you do it sooner, you risk a mid-meal walkout.

But honestly, we’re really saying this as people who like to go to restaurants. Don’t make us pretend we’re not wondering why that woman is sobbing while we wait for the bathroom.

Tell the truth (mostly). Some will disagree, but this isn’t the time for soul-baring honesty or trying to rationally explaining all that went wrong—getting too specific in a breakup is like telling your boss all the things you never liked about his “management style” on your last day. It might seem like it’ll feel good, but it’s a terrible idea.

You’re trying to make this as painless as possible. Which is to say, if you never told her you hate the way she eats pasta, great. Take that one with you to the grave.

Yep, band-aid and high-dive metaphors. Are they cliché? Yes, but that’s because they’re apt. Get it done. This conversation takes less time than it does to finish that coffee.* You’re not opening a negotiation, and it’s easier if you don’t make it sound like you are. One minute of small talk, a firm but gentle declaration, put a good bit of blame on yourself and then leave.

*This bit—in fact, all of this—is based on the idea that you’re young-ish and have been dating someone in the year-or-less range. If you guys co-own a Volvo, shut your browser and go think this through again. Then call your lawyer.

Stick to your guns. There’s no going back. Go drinking, tell strangers in bars about it, call your mom again, but stick to it.

It’ll be okay, we promise.