Choose your place wisely. Is it a weekday that’s not Thursday or Friday? Because any bar will do, unless it’s so crowded that you have to shout. Stay away from anyplace where groups of art school students arrive in herds and Instagram their mango-cilantro margaritas — they will take notes on their phones and incorporate the dialogue into their webseries.
Also stay away from places that have slow service. Right before I break up with someone in a bar, I think about all those movies and TV shows where a bartender protagonist has to step away to tend to an angry girlfriend/boyfriend or some other plot point as Tegan and Sara plays in the background, and I am stricken with fear that it will take forever to get drinks and the check. It’s like someone about to go into surgery, watching two doctors on Grey’s Anatomyhave a soap-opera fight while standing over a person whose chest is cut open.
Make it drinks, not dinner. For the love of all that’s holy. If you’re like “First let’s hold hands and spoon-feed each other couscous for an hour, then after dinner I’ll end it,” you are either Leopold or Loeb and seeya in hell.
It should be by whatever transportation you need to get home. Grease up that escape hatch and sliiiiide right in.
Show up early. You definitely want to be sitting and prepared for the conversation — it’ll throw you off if you show up late and frazzled and he’s already there, waiting. Just come like 15 minutes early and have one drink if you feel like it. No more than one, or else when he shows up, you’ll forget the censored version of your breakup speech (“I’m not in a place for a relationship right now” or “I just need to focus on myself/my job/my cockatoo”) and just blurt out the truth (“You can’t keep your penis hard,” “Your favorite show is Burn Notice, like your favorite show of ALL TIME.”)
Remember that dumping is sort of like a job interview — you need to present a certain version of yourself. In a job interview, when they’re like “What’s your biggest flaw?” you can’t really say “I show up to work hungover and have so much crippling anxiety about booking my boss’s hotel room and flight that I just hide forms in a drawer in my desk for months and hope I’m gone by the time they notice.” But you also can’t completely lie and say “I’m a perfectionist,” because that’s not true. We both know it’s just not. Basically, tell as much of the truth about why you want to end it as you can without hurting the person’s feelings to much. And make your reasoning mostly about you so you don’t antagonize the person.
Do not mince words. Rip it off like a Band-Aid. “I don’t think we should see each other anymore” is pretty effective, although I’ve also found that “I have contagious old-timey hooker crotch rot” cuts the need for explanation by half.
Do not be fazed by how the person reacts. Stand your ground, even if they look like a hapless kitten staring into the oncoming light of a tractor-trailer, which is very likely.
Dip as soon as you can. Since this is very likely the last conversation with this guy that you will ever have, and he is also half-hoping that you will get hammered enough to have sad but vigorous Bruce Springsteen-singing-“Glory Days”-esque Final Sex with him. Finish your drink, say “I should get out of here,” and book it to train that is super-conveniently nearby because you took my genius advice. Or go to J.Crew, it doesn’t really matter.
Don’t offer to stay friends. We all know how it is when we like someone who just wants to “be friends.” Learn from past gut-wrenching encounters in which you have been in their shoes, and don’t assume you can seamlessly transition into one of those sad, one-sided platonic things where you go to brunch with him when your friends bail and he becomes your longing, neutered “really sweet guy friend” who tells you that you look great in that shirt and gazes too long at your face when you get high and doze off on his couch. If it happens way later on, it happens — but right now it’s too fresh off the breakup to be healthy.