The Second-Hardest Part of Breaking Up Is Actually Doing It (Part 1)

We’ve all been there. You’re seeing someone and you’ve decided, for whatever reason, that you want out.

But once you’ve made the decision to break it off, you have a second logistical nightmare on your hands: how, exactly, do you go about breaking another person’s heart?

OK, it doesn’t have to be that dramatic. And to help you out, we’ll break it down, in order of descending difficulty.

First scenario: the guy from OK Cupid

You went out with StudlyDolittle69 once (or twice, or thrice), and no matter how hard you try to ignore it, that bald spot and lazy eye combo just aren’t doing it for you. But he’s treated you to a few dinners, and you feel bad…

The great thing about online dating is that it establishes electronic messaging as the standard form of communication. So even if you have his number, you only owe him an email/message.

Wait until he tries to contact you. Maybe the “this isn’t working” feeling is mutual, and, if you never hear from him again, you never have to tell him you’re just not that into him.

But if he does ask you out again, keep it short and vague. Say something like, “I had a great time with you, and I think you’re really cool. But I’m not really sure I’m ready to get involved with someone right now.” If he calls you and you want to have that convo over the phone, great. If he calls and you’d rather fire off an e-mail, that’s fine too.

If you really hit it off as friends (and, as weird as that sounds, sites like OK Cupid that try to match you up with someone based on interests often spawn just as many platonic friendships as they do relationships), you might say something like, “Your stories about your French host family had me laughing for days, and I’d still love to hang out as friends, if you think I’m friend material.”

If he responds with anything other than “Yeah, let’s be friends,” ignore him. He might ask you what went wrong. He might ask you to refund your half of the dinners. Whatever it is, you don’t owe him a response, and if he seems like he might be inclined to message again, block him.

It’s tempting to think, “Oh, if I just explain that it wasn’t about his personality, it was just about his receding hairline and wandering eye, he’ll feel so much better!” But the longer you drag it out, the less fair it is to him. When a guy asks why you felt like it wasn’t going to work and you gave him a straight answer, you might think you’re just clarifying, but what you’re really doing is giving him hope.

And no one wants to hear that he’s bossy, or that he talks too much about himself, or that he smelled so bad you had to breathe through your nose.

“But the odor’s such an easy fix!” you say. “And if I tell him now, maybe he’ll have better luck with the next girl!”

It’s not your place, and when you say, “If you try bathing more frequently, maybe you’ll have a better shot with the next girl,” he might hear, “If you try bathing more frequently,  I’ll go out with you again.”

And besides, would you want a guy telling you it wasn’t you, it was your waistline?

And we can’t believe we have to say this, but we will: if you’ve been messaging some guy and he drops his prostitution habit/bed-wetting problems/”I’m still in love with my ex,” do NOT send him a break-up message. Just stop responding.