The Hook Up: 7-6-2011


My dilemma involves a woman I’ve been friends with for about a year. We met through a mutual friend during a time when we had both recently broken up with long-term partners. However, I was immediately interested in her personally and also very physically attracted to her. That summer, we had (drunk) sex a few times. In a very direct manner, I expressed interest in dating her several times, but she indicated she wasn’t ready to start dating yet — or wasn’t interested in dating me. It wasn’t entirely clear.

In the year since we met, we’ve become good friends, and it’s a friendship I value greatly. Interestingly, our conversations have often revolved around the topics of dating, sex, really anything mutually titillating. Sometimes the focus of our conversations has seemed like a form of subtle flirtation; other times I think that’s just what we like to talk about. Needless to say, I hadn’t entirely given up on the idea of pursuing something more than a friendship with her, and I could tell it was at least somewhat mutual. So I wasn’t totally surprised when I went to meet her and some friends at a bar tonight, and we almost immediately started kissing. She sort of (again, drunkenly) challenged me on the status of our current friendship, indicating it was obvious that we should be sleeping together. But, lest another drunken one-night-stand confuse the friendship we’ve been pursuing, I let her friend take her home.

As I said, I genuinely value our friendship as it stands. I am also genuinely interested in being more than friends with her and I’m still not sure if her interest in me as something more than friends is just something she likes to entertain when she’s had a few drinks. She’s hot as hell, dynamite in bed, and her intellect and talent impresses me to no end. I don’t need to know right now that we’re meant to be girlfriends or anything, but I’m not interested in turning our friendship into a friendship with benefits. I’d like some assurance that it’s not a totally casual thing before I pursue a sexual or romantic involvement. How do I find out if she’s really interested in me as a person she could potentially date, or just seeking something fun for now? – Seriously For Real

Anna says: They say actions speak louder than words, but you know what speaks even louder than that? Drunks. And drunks can never be trusted, especially in matters of the heart, or any arguments involving the lyrics to Iron Butterfly’s “Inna Gada Davida.”

The most telling part of your letter is that the flirtation/sex only occur when booze is involved. You’ve been direct with her (more than once) and she responded in a wishy-washy way, which is, I’m sad to say, another way of saying “No thanks.”

Relationships are complicated, but they’re also sometimes far more simple than we like to admit. In your case, I would take her sober behavior to be more indicative of her feelings toward you, that of friendship. The fact that you talk about sex regularly is probably more a case of mutual comfort levels than anything lascivious. I mean, unless you’re, like, exchanging dirty texts and favorite porn sites or something.

I feel for you though. Friendships that involve sometimes-sex can get murky really quickly. Once certain boundaries are crossed, the potential for them to cross endlessly also arises, and you can never be sure if the changes in your relationship are a product of natural progression or simply one too many keg stands.

Also, such friendship+ situations basically thrive on mixed messages. The only way to confront the confusion is head on, with as much (gentle) honesty as possible. If you’re not into the idea of a friends-with-benefits situation, then tell her that. And make sure she is stone-cold sober when you do. Drunks have a tendency to forget important conversations while incapacitated. She might not even know what y’all discussed the last time you were together. If slippery boundaries aren’t doin’ it for you, then by all means, don’t allow them. Put the kibosh on drunken kisses or too “friendly” advances if that’s something you find frustrating or unacceptable.

One last thing, don’t take her hot-cold behavior as a reflection of your desirability. You are clearly a whipsmart, articulate gal who knows what she wants. Plus, you give good email. I’m sure legions of girls would be thrilled to drink you in without, you know, drinking you under the table.

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