I have a problem and need an outside party’s advice. I have this friend, “Joan,” whom I’ve known about four years. We’re very good friends and hang out on a regular basis. We always have a great time together because we have similar interests (snowboarding, running, music, etc.), and all our mutual friends think we should be together. A few years ago we even made out a little, but it never went anywhere.
The problem now is that she is in a relationship. Her boyfriend is a complete douchebag. None of our friends like him, and most of them have told me they think she and I should be together.
He’s moving out-of-state in three months, and she’s not going with him. They’re planning to try the long-distance thing, but I get the impression she doesn’t think it’ll work. So my question is, how do I proceed? My current plan is to sit back and wait for it to fail, but in the meantime I’m not getting any, which sucks. Should I tell her how I feel, or should I just wait? If I wait and it falls apart, do I swoop right in or give her some time?
—Stuck in a Holding Pattern
Do you really think waiting around for a relationship to fail is an effective method of getting what you want? What kind of crazy books are you reading that give that kind of advice? Certainly not mine (How Not to Date, available in fine bookstores everywhere).
Seattle men have a reputation for being passive pantywaists in the passion department. I get so many letters from women complaining about you guys and your noncommittal, apathetic approach to romance that I don’t even bother running them anymore. And you, my friend, sound like the poster boy for this rather unappealing stereotype.
So let’s see a little action here, shall we? Normally I advise against pursuing someone already enmeshed in a relationship, but it sounds like this one is almost over anyway. So here is what I prescribe:
• Keep it light, but tell her how you feel. By “keeping it light,” I mean do not make a big fucking deal out of it. One night when you two are out (alone), enjoying one of the many activities you enjoy together, say something like “When are you going to dump that loser and go out with me?” or “What an awesome 18-mile run—wanna make out?” This way, if she says something totally humiliating in reply, you can always claim you’re just joking without losing too much face.
• But if she blushes or flirts back in response, you’re going to have to man up a bit. This may mean moving in for a kiss, or it may just entail ‘fessing up to your feelings. As I will not be there to guide you, you’re going to have to let the situation and your intuition dictate what happens. Ignore the overwhelming urge to piss yourself in fear.
• If you get the idea that she is not interested, back off and move on. Don’t be mad at her because she’s not into you. I mention this because your letter has an undercurrent of anger commonly found in the emotionally constipated. It’s not her fault that she’s not a mind reader, nor is she obligated to want to date you just because all your friends think you’d be perfect together. Maybe that makeout didn’t go anywhere for a reason. Whatever you do, do not wait out the demise of their relationship—for one thing, because it may never happen.
Bear in mind that there is every chance in the world that, following this course of action, you may be utterly humiliated. However, most things worth having require some amount of risk. And if you fail, so what? Contrary to what you might believe, mortification is not a fatal condition.