Dear E. Jean: Whenever I meet a girl I don’t know, I suffer from truly spectacular social awkwardness. It’s difficult for me to function at any level, including breathing. The result: I’m 40 and I’ve never had a girlfriend. Never even come close. I’ve gone out on three dates in my life—each one a disaster. It didn’t help that I lived at home into my mid-thirties—way too long, I now realize. I’m trying to change my life. I’ve moved out, bought a house, and been working hard to overcome my shyness. I’ve begun having conversations with people I don’t know well. To my immense relief, I’m getting better with practice.
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So the question is, now that I’m working up the courage to begin dating, how and when do I tell someone about my odd case history without throwing them for a loop or turning them off completely? Yes, I’m also worried that I’ll make every other dating faux pas in the book, but one problem at a time. (Please, please, please, no “40-Year-Old Virgin” jokes.) —Self-Conscious Enough As It Is
Self, my swordsman: I beg your pardon. Did you say…three? Only three disasters, sir? Hell, there are hundreds of social catastrophes for you to enjoy. Get ready. Here’s your Not for Sissies Sun-tzu Battle Plan:
1. Lay Plans Go to your local church and sign an “abstinence pledge.” Statistics show you will lose your virginity within seconds after leaving the building.
2. Know Your Weak Points Don’t date. It will kill your social life.
3. Vary Your Tactics Instead, go to Meetup.com. It’s genius! Scroll through the dozens of inspiring, eggheady, world-bettering get-togethers in your area and choose a group that you like. (Yes, there are “Virgins” Meetups, not to mention “Beltway Atheists.”) And if you don’t join a group that is at least half female, I’m going to come to your town and hold a Meetup called “Bang Jim.” Then all you have to do is show up. Shake hands. Share a beer. No pressure. Make friends of all ages and both sexes.
4. Wage the PR War Your story: Single guy, a bit shy, good job, owns his own home, no baggage.
5. Allow Yourself to Be Conquered And when you get effed up and shaky in the middle of a conversation—excellent! Most young ladies will walk over their own grandmothers to find a man who will listen to them. (Sun-tzu says the warrior who “gathers the highest intelligence” achieves the “greatest results.”) So don’t worry. Wear something handsome, look her in the eye, ask a question, listen, throw out a compliment, ask another question, and in a few weeks you’ll be poking like blazes! Good luck!
This letter is from the E. Jean archive.