I’m a 33-year-old, confident single gal who often dishes out dating advice to my friends. Over the past six months I’ve developed a friendship with "Mr. M,” 12 years my senior, and it became evident that we share amazing chemistry. I’m extremely attracted to him. Trouble is, I want to be in a committed relationship. Mr. M’s divorce ended badly, and he clearly harbors bitterness towards marriage; he also admits to having issues with even non-marital commitments. But he’s extremely fun to be around and we always have a wonderful time. On two separate occasions, after a long evening of dinner, wine and flowing conversation, we hooked up. I realize he can’t offer the relationship I want, so am I playing with fire by sleeping with him? By crossing that line have I pigeoned-holed us as "friends with benefits"? I thought I was long over my attraction to unavailable men. I am open to meeting and dating someone else. but I have such a weakness for Mr. M. Am I doomed?

He Said: It doesn’t sound like you’re over your attraction to unavailable men to me. You’re certainly not doomed however; you can redefine your relationship without his permission and pop out of your pigeonhole even if he likes it there. Your dilemma is that the more you enjoy the company and occasional hookup with this guy, the more attached you will become, and the less likely you’ll put energy into finding someone who is interested in building a committed relationship. Certainly if you harbor any desire for having kids, you should be spending less time with this guy.

But regardless of what types of hormones are inspiring you, in any relationship one person puts in more energy than the other and right now you are that person. Focus your energy elsewhere, maybe dating other people, maybe just enjoying time alone or with your friends. This guy might surprise you by stepping up, but even if he doesn’t, you’ll be in a better position to find someone who’s available.

She Said: Well, I agree with the advice above, but just so we explore both sides of the coin, here’s another angle. What if you kept seeing Mr. M but also stepped up your dating life? This is a dilemma a lot of singles find themselves in, and I’ve seen both strategies work. Cutting off the unavailable man cold turkey and pouring energy into dating others may be good, as long as the obsession you feel about not seeing Mr. M doesn’t weight you down more than seeing him does.

Your other option is to space out your dates with Mr. M so that you keep a nice flow of friendship, fun, conversation, and sex that can “tide you over” until you find a serious relationship. But for this approach, you need, as they call it, a strong pipeline full of dates, social activities, sex and fun outside of M. so that you stay open and ready for what you really want.

Of course, you realize that both these strategies involve the same tricky twist: Both make you more unavailable to Mr. M, which makes him desire you more and possibly chase you more, which throws a wrench into the whole thing because his feelings might change, or his feelings might appear to change. As might yours. But choose one of these first steps and see what happens.

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