HEY CHIRL: I Want to Be a Top But My Boyfriend Won’t Let Me

Our columnist, Twink St. Pine, solves your love conundrums.

I’ve been, shall we say, at the bottom of things for my entire three-year relationship, but lately I’m wondering about what it would be like to be tops. Problem is, the boyfriend has made it clear he wants no part of a swap. Should I just forget it?

Chirl, negotiating sex is like cutting the federal deficit: Everybody thinks it’s a good idea until you start actually suggesting things. Your problem isn’t actually about sex—it’s about being flexible (and I’m not talking about the cowboy position). Unwillingness to compromise almost always leads to resentment, something I can testify to every time my Arthur refuses to hand over the black Amex. If your guy can’t be open-mind­ed enough to simply try something new in the sack, he risks you eventually giving him the sack.

Settle this: On first dates, who pays?

Chirl, the safest rule is this: On first dates, you split it, whether it’s coffee or a five-course meal at Vetri. (Side note: Do not agree to split a five-course meal at Vetri on a first date unless date looks like Darren Criss. Or perhaps is Darren Criss.)

Is there one ideal place to meet guys?

Chirl, as decried as it may be, the standard gay bar offers instant eye contact and appraisal, a safe atmosphere to chat without too much pressure, and … booze. A gay interest group can offer similar opportunities (PhillyGayCalendar lists a bunch) without the Manhunt-y vibe. Of course, I met Arthur at that other gay mecca, Nordstrom. I said to myself, Any man buying that much Lilly Pulitzer is worth knowing. 

I’ve been dating a new guy. He’s perfect: Good job, nice digs, great kisser. But he dresses like a 12-year-old—he wears track pants to restaurants! I’ve been subtly buying him new clothes, but he doesn’t seem to be biting. Help.

Chirl, making over your boyfriend is the same as wearing sandals to work: Sounds eminently doable, but it’s fraught with danger. Your best bet is to take the long view: Compliment him wildly when he dons something you like, buy him stuff you like but throw in a t-shirt you know he’ll love, and occasionally rip off his clothes for some lovin’ when he’s wearing something good (“You just look so hot in that …”). Nothing reinforces good behavior like good sex.

I’m white, but I date African-American men almost exclusively; I just tend to be most attracted to them. But you wouldn’t believe the crap I take from my friends about it. Am I doing something wrong?

Chirl, first off: Who are your friends—the local frat? Sounds like a shake-up in your social circle may be in order. Surely some of them prefer blonds, or short guys, or buff guys, and no one says a word about it. We all have different things that get our engines revving—the hair, the eyes, the teeth, the pecs, the 401K. Stop apologizing for yours.

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