Tough Love

Our new dating-advice column will whip your relationship into shape.

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Illustration: Gaia Cornwall

Q

My boyfriend and I have been together for almost seven years (since college). For the most part, things are good; we live together, don't fight, etc. I'm not bride-crazy or anything, but I always figured I'd get married someday. Everyone assumes that we will. But for years he's put it on the back burner when I've brought it up, said he wasn't ready yet. I gave it time, but nothing's changed in, like, four years.

So I've been thinking of giving him an ultimatum—propose by a year from now, or we're done. Is that reasonable?

A

An ultimatum is reasonable, I guess, if you really want to get engaged by a specific date. It is, however, final, by its very definition, so before you come in with the heavy artillery with your boyfriend, have a conversation with yourself first.

What is the rush here for you? Do you feel like, after seven years, you "should have" kicked it up a notch? Are you worried that if you don't set the wheels of married life in motion, you'll run out of time to have kids? Is the siren song of crystal and fancy blenders calling to you, irresistibly, from your Amazon wish list?

None of those concerns are wrong or bad. Transforming any of them into an ultimatum is dicey, though, because you put your boyfriend in the position of obeying you or else. If it's the guy you want, you may have to make your peace with a less literal commitment. Some guys do respond to blunt ultimatums—but unfortunately the response may be, "Fuck off," and where does that leave you? Packing up and moving out; if you make the threat, you'll have to follow through.

You don't have to make it so adversarial. Figure out what you want and ask your boyfriend for it. Discuss a timeline. Give him a chance to work with you. Tempt him with a vision of new cookware.

Or grab a Ring Pop and propose to him. It's 2010.

Q

I'm 27 and happily single, but recently my best friend (a quite attractive guy) told me he's secretly in love with me. And then we made out—at the time, we were really drunk. Then he avoided my calls for the next week. This gave me time to realize I am probably in love with him, too. When I finally cornered him at a party, he told me he is messed up. He meant what he said, but he wants to "forget it ever happened" and go back to the way things were because he's not ready to deal with it. What should I do?

A

I have good news and bad news. The bad news is that when a guy utters any variation on what your best friend said to you—I'm messed up, I can't be in a relationship right now, I don't want to ruin the friendship—you must take him at his word, and you must run, or at least walk briskly, in the other direction.

When people do you the courtesy of telling you right up front that they can't (or won't) make it work romantically, you must, must believe them and move on. Pushing your best friend into something he's not ready for can only end badly; either he continues resisting a relationship, which will hurt you, or he tries to give you what you want because he cares for you, but then he freaks out later and bails after you've gotten attached, which will also hurt you.

It sucks. It sucks doubly because of who he is. He's your best friend, but you can't vent to him about the situation, because he is the situation (but not, happily, the Situation, I assume).

It's maddening, it's not your fault, and I totally feel you, but the good news is that if you do nothing for a while—give your bestie space, and don't force the issue—things will work themselves out in one direction or the other. Maybe he'll realize that he's not that messed up and wants to give it a try as your boyfriend. Or maybe you'll realize that he's not the one. In a few weeks' time, you'll know more.

Q

I got stood up for the first time last week. The guy has been apologizing, blaming alcohol and shit, but I can't seem to shake it. I waited for two hours on this bench where we were supposed to meet; he kept texting me like, "I'll be there soon, I promise," and it was, like, midnight. I'm on a fucking bench alone and he doesn't come. I was calling him and calling him and he didn't pick up, but would text me like, "Ahhh, so sorry, almost there." Now he's trying to make it up to me —but what would you do? Would you give him another chance? Am I being overdramatic?

A

"Give him another chance" to...what? Maroon you in an even more unsuitable location? Invite you for coffee in a dark alley? Drinks at the top of the Wonder Wheel? That'll do. Cut him loose. He's the one creating unnecessary drama here, not you.

First of all, if he's texting that he's "almost there" but never shows up and won't pick up the phone, he's with someone else. That, in itself, is not necessarily a big deal, but it became a douche move when he had no respect for your time or safety—for you, period. He should have just told you he couldn't make it, and let you get on with your night, but instead he strung you along and assumed you wouldn't put two and two together. I don't know how he could make up for treating you like you're a stupid pushover.

I'm sure he feels bad now, but it's too little too late. Stop taking his calls or texts; it's your least dramatic option.

What's wrong with your relationship? What's keeping you from even having one? Send your questions on matters of the heart—from making out to marriage—to toughlove@timeoutny.com.

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