Extreme Meek Over

I’ve been friends with a woman for five years. She had a boyfriend when we met, but they split two years ago. Due to a lack of confidence, I never formally asked her out, but I wanted to. Recently, another friend of hers made moves on her, and I realized I’d blown it. They’ve stopped dating, but it seems I’m not an option because she no longer returns my calls. Now, I lack the confidence even to try and contact her. Is there anything I can do?

--Waiting On A Friend

Oh, the trials and tribulations of the imaginary romance. You’ve spent five years of your life with this woman -- but only in your head. Of course you lack the confidence to contact her now. What are you going to say, that during imaginary sex with her, it’s possible you gave her an imaginary STD? When you’re 5, imaginary friends keep you from being lonely. When you’re 25, they keep you from having a life. At the moment, you’re well on your way to becoming that 50-something guy on my boyfriend’s block who’s always sputtering that he'll never be one of those chumps who pays for everything on a date. No, he won’t, because he’s unlikely to ever have one, since he’s too socially constipated to speak to any woman who isn’t a clerk at 7-11 selling him beer. Of course, there’s always that chance a lost hooker will get a flat on his street, see the light in his parents’ garage where he lives, and offer him a freebie in exchange for putting on her spare. Like this guy, you probably work hard to avoid acknowledging the existence of the weenie within; perhaps by clinging to helpful, action-stopping mantras like “good things come to those who wait.” Sure, they do -- if your idea of a “good thing” is the bus. No, women don’t make it easy for men. Just decades back, they’d flirt to signal to men that they could ask them out without being rejected or maced. These days, women often make it a complete mystery, or seem to be signaling at everybody at all times -- stopping just short of making lingering eye contact with a fire hydrant. How can you know for sure that a woman wants you? You can’t. If you want a woman, ask her out. If she says no, gather up the remains of your ego, glue them back together, and ask somebody else. Had you done this when this woman came back on the market, you’d either be dating her or you’d have moved on to become a real friend. Instead, you were the friend version of the “funny uncle,” pretending you had platonic intentions while secretly festering with lust. Think about what fun this must have been for her, always being on guard against those hugs that go on a little too long. What a surprise that she isn’t scampering back for more. In the future, categorize women when you meet them: “potential sex partner,” “probable friend,” or “not a chance.” Should a “potential sex partner” have a boyfriend, flirt subtly to tell her you’d be into her (if she’d just ditch the bum). In the meantime, avoid getting too chummy, listening to her boyfriend problems, or otherwise being “like a brother” to her, as it’s unlikely to catapult you into a relationship or her bed. Of course, it should leave you ample time to ponder important public health issues; say, whether having imaginary sex with somebody means you’re really having imaginary sex with everybody they’ve ever had sex with, real or imagined.