Hey Woody!

I’m a 23-year-old GWM — conventionally cute, a little shy, fairly intelligent, with my own unique personality… you know, all the usual nice stuff.  Here’s my problem… I think I’m turning un-gay.  Not STRAIGHT, mind you — I have no sexual attraction to women at all.  But I feel myself losing my attraction to men, especially gay men.

Over the past seven years I’ve dated quite a few men of various ages, backgrounds, ethnicities, etc., yet over these years I’ve never dated any one guy for longer than a few weeks.  Why?  Because the guys I date just seem to quickly degenerate from “nice” to “annoying/selfish/immature/needy.”   Here’s what usually happens: at the first few dates, Guy X will seem just fine, but after we get past the first getting-to-know-you weeks, Guy X becomes a slob.  Or a jerk.  Or a selfish prick.  Or a needy codependent. 

Now, I’m not an idiot.  I realize that there’s no such thing as a perfect guy.  But each time I’m dating Guy X and the problems begin to surface, the first thing I try to do is work THROUGH the problem with him.  What usually happens, however, is that Guy X puts ALL the weight of the problem on my shoulders, expecting me to either deal with it or solve it entirely on my own — and when this happens, I dump his a–.      

At this point I find myself almost entirely uncaring about even trying to date: I don’t update my online profiles anymore, or go to clubs or bars, and I generally avoid interacting with people outside my immediate circle of friends.  I feel afraid to try dating again because it’s never brought anything positive into my life.  So my question to you is — how do I deal with this?  The “keep trying” s–t I get from my friends was helpful for the first few years — but at this point it doesn’t work for me anymore.

– Skeptical and Losing Patience

Dear Skeptical:

Keep trying?  The only people I ever tell to “keep trying” are tricks trying to get my pants off when I’m too drunk to do it myself.

The only thing I’d “try” if I were you is fixing your awful personality.  Your email drips with so much judgment, cynicism and negativity I had to towel off my screen when I read it.

Take a good hard look at your letter and ask yourself:  “Would I want to date this guy?”  I wouldn’t.  You’ve got “BITTER VICTIM” written all over you.  The only common denominator in all your dating failures is YOU and yet you blame everyone else.  “Keep Trying?”  Please.  You need a personality over-haul.  Here’s how to start:

  1. Don’t Point. Point the blame at someone else and there are three fingers pointing back at you. I don’t doubt these guys had their issues but it’s far more valuable to ask yourself, “What role did I play in this?”  Take some responsibility.
  1. Switch the Question. You know which one I’m talking about—*“Why can’t I find quality guys to date?”* The real question is, “Am I a quality guy to date?”  Hint:  Look at your letter.  You have no power if you think everyone around you sucks.  But if you think YOU suck (and you do) then you have the power to change that.  Un-suck yourself and you’ll attract stable guys.
  1. Ditch the cynicism. There are two kinds of guys: The kind who ask, “Can I buy you a drink?”  and the kind who ask, “Can I buy you a drink or do you just want the money?”   The point:  cynicism has a way of repelling decent guys.  You can avoid cynicism the way baseball players do—by reframing failures.  Ask any great professional baseseball player.  They think every strikeout brings them closer to hitting a home run.