The Hook Up: How do you bounce back after difficult times?

I’ve been seeing this woman for a few months now. She’s one of those swaggering, leather jacket-wearing lesbians that oozes confidence and has a well-known reputation as a player. We’ve been hooking up for sex, and that’s the extent of our relationship, but I think I’m falling for her and I hate myself for it. But when we’re together her reputation and presence just don’t add up. She’s giving in bed and so thoughtful, remembering things I’ve said and little details (and SO cuddly). She layered and talks about fricking Virginia Woolf for goodness sake. She uses “sir” and “ma’am” to talk to complete strangers and waves at babies in prams, but at the same time I hear all these stories of girls she’s screwed over, cheated on, etc. She’s even admitted it to me and doesn’t seem at all remorseful. She describes herself as “a bit of a dick” but I know from being with her that that’s just not true. She’s a walking contradiction. My friend’s think she’s bad news but I can’t help myself.—Sent From Windows Mail

Anna says: Are leathered lesbians supposed to hate babies? Is that a thing? Because I think most of us—even the toughest, badassest, Navy SEALs, shark-wrestling biker-pirates—still think puppies are cute, you know? We are allowed to like Virginia Woolf AND Pat Califia, Sent, to be both thoughtful and selfish in bed, to enjoy cuddling and steel-toed boots. Humans are contradictions, all of us. That’s basically the definition of humanity. So let’s worry less about her “reputation” as it were (though you should probably always listen when someone tells you they are a dick), and focus instead on your relationship.

You started casual but now feelings are involved. (Look, another contradiction!) There’s no need to hate yourself for your newfound falling-feelings. Falling-feelings are good! You like her. You’re smitten even. Buuuut, those feelings happen to lie outside your pre-approved agreement for Just The Sex Please. So. You have two choices. Well, three actually. You can squelch those love-feelings, pretend like you’re fine with the no-strings-attached agreement, and hope your crush passes. Or, you can tell your hot, leathered lady that while you didn’t plan it, a feelings garden has sprouted in your chest, and what do you say, do you want to explore that? Or, you can stop sleeping with her, end your casual arrangement, and seek out another lady altogether who wants the whole sex-feelings package and doesn’t compare herself to a wang.

I vote for option number two, personally. It’s the riskier one, especially if you don’t want to give up the sexytimes, but it’s also the most honest one, and potentially has the biggest payoff. It’s up to you, of course. It’s also quite possible that your crush will pass, given enough time and possibilities for you to witness her dickishness first-hand. If she really is a tiny penis, it will be revealed eventually, and it sounds like it has a little already, what with the cheating and the no-remorse business. Here in Hook Up Land, we are big fans of directness and truth-telling, even when it’s awkward and awful in the short-term. Besides, maybe she has feelings for you as well, and wants to make babies that she will then smile at because babies are cute. You never know until you ask.

Will you? Prove you’re most badass of all and tell your Harley Hottie that you’d like to cuddle with her on the regular.

p.s. And while we’re at it, was this a typo? “She layered and talks about fricking Virginia Woolf for goodness sake.” Or is layering the new tough thing? Or did you mean lawyered, like she got a lawyer to follow her around so as to appear more intimidating? I have a lot of questions this week, it seems.

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a freelance writer living in San Francisco. Find her at and on Twitter @annapulley. Send her your The Hook Up questions at   


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