I realize this probably isn't the most interesting question, but I figure since it's one of those things they always seem to be writing about in Seventeen and Cosmo, I can ask you. I have developed serious feelings for a very good friend of mine. In the past, we have had brief sexual encounters that were later shrugged off as being drunken or hormonal.
Honestly, the experiences in the past didn't mean anything, but now I find myself looking at him in a completely new light. What can I do to show him that I am interested in him, and not just for a little booty? I think we could really have something, but he's kind of skittish when it comes to relationships, so I think the direct approach would only freak him out. What would be the best long-term plan of action?
Ah, the old friend/lover conundrum . . . I know it well. I was originally going to call a bunch of my boy friends and tell them I'd fallen deeply in love with them just to gauge their reactions, but frankly I was afraid of what those reactions might be. So let me tell you a little story instead. It happened many years ago when I was a struggling young editorial assistant. . . .
As the managing editor took me around my new workplace, introducing me to the various mooks who ran the magazine, everyone kept saying the same thing upon meeting me. "So you're sharing an office with Lou?" Then they'd laugh. Hard. By the time I'd met everybody, I was extremely paranoid. When I finally met Lou—the office curmudgeon and an all-around cranky guy—I was not impressed. For one thing, he was 12 years older than me and looked it. He wore his hair short in the front with a straggly long ponytail hanging down the back. Color me shallow, but this hair-don't skeeved me beyond words. He had a beard (eww), large Greek nose (his only plus in my book), and tended to dress monochromatically but uniformly horribly. And then there was the fanny pack.
Anyway, we were forced to share a small, windowless office. Much to my surprise, he grew on me. He was smart and very cynical, but with a soft side that few saw. We became pretty good friends and eventually—much to my dismay—I discovered I was in love with him! I was in love with a middle-aged man with a rat-tail! The horror!
But I couldn't tell him. Like your boy, Lou was extremely skittish about getting involved with anyone. Or at least that's what he kept telling me. He was also painfully oblivious to my obvious infatuation with him. Then one day he rolled in and told me about this cute girl he'd met the night before. Before I could stop myself, I snarled, "Did you fuck her?!" He looked shocked, and then the lightbulb went on in his head. Ding!
A week or two later found us nervously sitting on my sofa, pretending to watch TV. He turned to me and said those romantic words that most girls only dream of hearing: "You wanna keep this clean or what?"
We were together for six years, and then he dumped me and died shortly thereafter. But that's a whole 'nother story. The moral of my tale is that sometimes it works out. For a while anyway.
Now, what to do. First off, whether or not he wants to admit it, he is already in a relationship with you. You are Friends Who Fuck.Whether he is willing to evolve your relationship into Friends Who Fuck on a Regular Basis is what remains to be seen.
You could just wait it out like I did, but that would be a foolish waste of time. I know it's scary to be direct, but it is possible to phrase your feelings and wants delicately. I do not recommend going the route of blatant manipulation and lies. For one thing, I know I always end up loathing he who is easily manipulated. For another, that kind of web-spinning is dull—wouldn't your time be better spent reading a book or enjoying refreshing beverages with friends? Leave that kind of shit to the kind of women we hate. Either Studboy wants to be your man or he doesn't. Believe me, honey, you do not want to get involved with someone who's only there because you tricked him into it. You should simply point out to him that he'd be insane to let a gem like you slip through his fingers. And if he still resists your charms? Well, that's no reason to end a lovely friendship, but I would remove the "Fuck" from the "Friends Who" description.
She can help. Ask firstname.lastname@example.org or Dategirl, c/o Seattle Weekly, 1008 Western, Ste. 300, Seattle WA 98104.