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Roommate Crush...Virgin Holdouts

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Q: You know that stock character in the movies, the hot-to-trot divorcée who’s “hitting her sexual peak” in her fifties and won’t shut up about it? That’s my mother. Now that Dad’s out of the picture (and for my own sanity, I’ve always preferred to think they had sex just the one time required to conceive me), she gives me the gory details about every Tom, Dick, and Fabio. I guess I’m glad she’s having fun, but yuck. I know her: If I ask her to stop, she’ll get all wounded and say I’m “not supportive.” Help!
—DISGUSTED DAUGHTER, INWOOD

A: At least you’re in a better position than the daughter in that British movie The Mother, who winds up shagging the same bloke as her mom. In any case, it sounds like your mother, social/sexual butterfly though she may be, is lonely. And you are her daughter, not her best friend forever. Bottom line: She needs friends her own age. So instead of directly shutting down her sharing, support her in finding other outlets for girl talk (a dirty-book club, maybe)? Chances are, when she finds more peers’ ears to bend, she’ll give you a break. (Unfortunately, though, the technology doesn’t exist yet to erase, Eternal Sunshine– style, all memories of what you’ve already heard.)

Q: I think my roommate is after me. We went to a bar the other night and she was kind of touchy-feely, and tonight at the movies, I noticed her slouching and scooting closer. I’m definitely interested. Should I make a move?
—DO-ME ROOMIE, MINNEAPOLIS, MINN.

A: What is it with all you roommates? The Help Desk is beginning to mourn the demise of platonic cohabitation. What you need to ask yourself is whether what you have here is cuddling wrought of sexual chemistry or cuddling she might describe to her friends as “Wow, it’s so great being so comfortable with a guy—it’s like I can completely trust him not to make a move because we are just soooo on the same wavelength!” So next time you’re getting drunk together and snuggling, try to kiss her. If she says “Finally!,” you’re in. But it may be wise to start scanning the apartment listings in advance in case she recoils in horror.

Q: I’m 26, and I’m a virgin. You’d never guess from looking at me or my Palm pilot: I don’t go to church (and not just because I’ve been at Crobar till 4 on Sunday morning), I wear stilettos, I smoke. I suppose I’m a late bloomer and just haven’t met the right guy—until now. I’ve been seeing him for a few months and feel like he could be the one to make a dishonest woman out of me. But he has no idea he’d be my first. And the longer I wait to tell him, the weirder and harder it gets. How can I just get this over with?
—READY FOR BEDDING, MURRAY HILL

A: The Manolos and cigarettes and $12 cocktails came easy when you were saving all that money on birth control, right? Not anymore! As you seem to understand, the less you think of sex as casual, the more, well, formal it gets. And harder to see for what it is: neither meaningless nor divine but somewhere in between—a pretty big deal, let’s say. High-school-health-class glib as it may sound, if he really likes you, he’ll understand. So tell him at once—it will likely turn out not to be the giant deal it’s become in your mind. Especially if you’re wearing just your stilettos and a smile.

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