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Dear Breakup Girl,

The Question: What can I do at 26 to build up confidence in dating and relationships?

My situation: I'm in a bit of an awkward position. I'm a guy in my mid-twenties and I have very little experience dating or with women in general. In high school and through part of college most of it stemmed from a lack of self-worth and an inability or refusal on my part to trust people. There was never a lack of interest, I just don't think I had what it took then to ask a woman out. Nowadays, things have changed. I get along well with my family members. I have a decent career plan mapped out and I'm purusing and reaching most of my goals. I'll soon be enrolled in a MA program. I earn a nice living and I'm financially stable. I own a condo and a car. I have varied interests and I'm an active person. I work out, pay attention to my appearance, and consider myself to be attractive (female friends have described me as cute to their friends, great looking women occasionally approach me when I'm out on my own). I always do my best to act with integrity.

Today, as ridiculous as it sounds, I think most of my dating woes stem from worrying about what the particular woman I'm out with is going to think about my lack of experience (not just dating, but with relationships, intimacy and sex). I have a lot of residual lack-of-confidence. The end result is that I still have a *very* difficult time talking to women. Instead of always coming across as nervous or jittery or flakey as I might have in the past I'm considered to be "uptight." Nevertheless, I usually meet a decent number of women; friends, family-friends and acquaintances don't hesitate to set me up. Occasionally I'll meet a woman on my own intiative. If I'm approached in a club, bar, or some other social setting I don't do so well and usually shy away. My friends wind up busting my balls and asking me "What is wrong with you?!?!" or "You must be nuts!" the rest of the night. I typically end up kicking myself for the rest of the week and promising myself that it won't happen again. But it always does. Always. The few dates that I do go on usually don't wind up in the nightmarish category--I just wind up coming across as too quiet or unable to carry on a conversation, even though I'm dying to talk more. What should I do?

-- Mr. Pitiful

Dear Mr. P.,

Hmm. Either you're totally normal, or you're not. Ha, no wonder you hate talking to women! No, seriously. Either you have a case of garden-variety shyness that you've worried into a near-phobia, or it was a near-phobia to begin with. Also, it's possible that your stress and embarassment about being a virgin (right?) (not that there's anything wrong with that) has taken on a life of its own. Either way, there's some serious anxiety here -- and you won't let yourself off its hook.

If you want to start slow/small, try this book and let me know if it's helpful. If you want to start crass, yet possibly effective, please know that there are some very nice women out there with a Flo-Night thing who would be pleased to relieve you of what you perhaps consider your liability. And, of course, talking to a professional may help you uncover your problems with talking to, um, amateurs.Just because you've got [most of] your life together and your love life is short of nightmarish doesn't mean you don't qualify. Au contraire: your general togetherness and apparent non-total-freakitude makes your anxiety that much more compelling a topic.

Oh, and step one in Assertiveness Training: tell your friends you can bust your own balls perfectly well without their help, thanks.

Love,
Breakup Girl (with help from Belleruth)

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