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Roommate- and Ex-Sex
To bang or not to bang your roommate and how to negotiate sex with your ex.
Tuesday Jan 22, 2008.     By Anna Pulley
Centerstage Chicago Nightlife City Guide Arts

Dear Maven,

So, I've been apartment hunting in New York for the last couple weeks and I finally found a place that works for me. It's a great apartment, nice location, affordable. But the thing is, my new roommate is incredibly sexy. I'm not sure living with this person would be a good thing, because if my feelings for her are not reciprocated, it could be very awkward. I love the apartment, though. I'd hate to leave it because of this. I'm fully aware of how silly this sounds, but seriously, she's amazing. What do I do?

Hank

A: Come now, it's not silly! If your roommate were a robot, then, yes, we'd all have a good chuckle at your expense (and by "we," I mean me and R2D2). Many a victim has fallen prey to the roommate crush. Now I've never lived in New York, but I'm still Jenny from the block-used to have a little now I have a...dating column. If there's one thing I know about New Yorkers, it's that they drink soda with straws, even when it comes in cans! If there's something else I know about 'em, it's that they are constantly looking for better apartments. If you've struck gold on this already, then ask yourself: Does the hotness of the aforementioned roommate supersede my potential homelessness? Be sure to factor in varying degrees of awkward bathroom conversations, possible humiliation and the state of our depressed economy before answering.

While dating one's roommate has many perks—convenience, cheaper rent, someone with whom to share the delightful melon-baller you bought from Urban Outfitters—you are treading in dangerous territory. Has she expressed some sort of interest in you? Offering you one soda with two straws perhaps? If she hasn't, then I would do what any healthy single male would do: repress, repress, repress! Be grateful that you get to experience the casual hotness in a close proximity that most men don't, but know that ultimately living with someone is bound to unearth their disgusting habits. If her used o.b. tampons and Little Mermaid flannel pajamas aren't enough to squelch those sexual urges, then I suggest you start listening to more Josh Groban.

Dear Maven,

I'm going to visit my ex-girlfriend in New York soon, and I was wondering how to broach the "friends with benefits" thing with her. We parted on friendly terms, and I'm only staying with her for a few days, so very low commitment. How can I bring this up without coming off as a douchebag?

Dave

A: Sex sex sex. That's all you people want from me! It's never, "Dear Anna, I need help with my alley oop" or "Tell me, what are the origins of the pan flute?" And when indeed I get those questions, "alley oop" and "pan flute" mean something else entirely.

When propositioning your ex for sex, I find it's generally helpful to not do it while playing charades. It's hard enough to pantomime AND remember which hand gesture means "syllable" without all the added sexual innuendo. Barring that, women are suckers for nostalgia. And props. Try talking to her about some of the great times you've had together, slowly adding in some of the sexual ones. If you have a hand puppet handy, use it. "Remember when you surprised me by pulling out that bit gag during 'Spiderman 2'? [Insert pipe cleaner rendition of Tobey Maguire] That was so sexy."

Of course, tell her how amazing she is, and that you cherish the connection you once had. Be careful, though, that she doesn't think you're trying to rekindle the relationship flame. God, did that backfire with my ex. I was like, "Look Beyonce, you're bootylicious and all, but I'm a survivor and I'm not gonna give up." Reiterate that it's a temporary thing and that, really, she's never going to do any better than you anyway, so she might as well tap that ass one more sweet, glorious time before you move on with your life and forget about her entirely. I have a great hand puppet for that, FYI.

Anna Pulley, our Meet-Market Maven, has been on more bad dates than J. Lo's been to divorce court. She's been a one-date wonder and Wonder Woman. She's bi, and no she doesn't want to sleep with your boyfriend, thanks. When she's not giving advice, she enjoys theme parties for every and any occasion and working as a Carnal Consultant for Early to Bed. Buy her a drink or ask her a question already.