Tough Love: She's hot for her roommate. Should she confess?

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Q:

I've been dating a guy for a few months. I don't really want a serious lifelong commitment (right now), but I do feel strongly about this person. I want to know if we're going to "do" the monogamous relationship thing, or if he sees this as a casual fling. How should I broach the subject with him, or is it too soon?

A:

I don't think it's too soon—"a few months" into a relationship is usually the point when you move forward or move on. But before you have the DTR (define-the-relationship) talk, you should consider some things yourself: what you want now, what you want in the future and whether you want whatever it is from this specific guy.

So what do you want? Do you want a monogamous relationship but worry that he'll think you want to get married and settle down? Does it seem like he has the same strong feelings for you—or are his too strong for your comfort? Or do you think he doesn't care that much, and that scares you?

I do get the sense that it's commitment you have doubts about, not the guy, and I want to remind you that agreeing to monogamy doesn't automatically consign you to a princess wedding and a bunch of babies. It's not a prison term; if you decide to get exclusive but it's really chafing after a month or two, you can throttle things back to casual-fling status, or break up.

By all means, talk to him, but be honest with yourself first: Figure out what you're after before you ask him the same.

Q:

I hate condoms. I think everyone does. But that's beside the point, because lately I have been hooking up with a friend, and every time we get to the whole condom part of the deal, he loses it. Even when he can sustain some hardness, he still can't orgasm when he is all wrapped up. I want to keep having sex with him because everything else is wonderful, but condoms are really holding back the magic. Help!

A:

I take it you've exhausted every possible condom option—every brand, every thickness, every lubricant. One size does not fit all when it comes to jimmy hats, so if you two haven't made a game out of testing the various sizes and flavors, I'd start there. Go on a buying spree at Duane Reade; better yet, head to the Gay Men's Health Crisis (gmhc.org) or a sex-positive shop like Toys in Babeland (babeland.com) and ask for advice. This is an extremely common complaint, and people who deal with it for a living will surely have some fantastic suggestions for staying hard and safe at the same time.

If your buddy still can't go the distance with the Barely There Hot Sauce Sausage Slicker [Ed. note: not a real product...yet], maybe it's time for you both to get tested for STDs; agree not to sleep with other people; and proceed, condomless, as you use another form of birth control like the pill or the sponge. That might feel too coupley for you (my GYN actually calls that blood-work series "the boyfriend test"), and those other forms of pregnancy prevention fall in the woman's lap; you may not want to go there, emotionally or medically.

Then again, he's your friend and you're obviously having a fair amount of good sex; you could give the relationship thing a shot. Just something to consider.

Q:

I live with three roommates, and a few months ago I started to develop feelings for one of them. We've gotten to be pretty good friends and run in the same social circles. It seems like his interests parallel mine most of the time. I've tried to distract myself from being into him, but I can't stop thinking about him in a romantic way. Is it worth saying anything? And if so, what is the best way to approach this without being a sleaze?

A:

I would not approach it at all until one of you has chosen to move out. First of all, you've developed feelings for him, but you don't mention whether he might share those feelings for you, which is not something people forget to bring up in this situation. So, either you can't tell whether he's crushing on you in return, or...he isn't. I'm sorry to tell you that scenario is more likely. You've become friends with the guy, you live together. You'd know by now if he felt the same way.

So, if he doesn't return your affections and you sit him down for a big discussion about it, it's awkward—for you, for him and for your other roommates who will inevitably pick up on the weirdness between you. That kind of thing will pass, eventually, but until it does, you have an uncomfortable couple of months in your own home.

Another ugly possibility is that he does like you That Way and it does work out—until it doesn't, and then you break up, and then you can multiply the aforementioned circumstances by, like, a tear-and-wine-soaked thousand. And one of you will probably have to move out. Resentment! Heartbreak! Skip it, please! I know I sound really pessimistic and discouraging, and I also know it's really hard to make yourself stop crushing on a guy you see every day, but I have seen the intra-apartment romance work out long-term only once. One time. Give yourself five to ten minutes a day to moon over Mr. Second Bedroom, then think about something else. It'll pass, and in a few months you'll be so relieved that it did.

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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