The Mold And The Beautiful

I'm always amazed when I hear how the smooth guys at my office pick up women who are total strangers. I know it's best to meet dates through friends or shared interests, but sometimes I'll spot women who look like my type in the supermarket or on the street. I'll think about asking them out, but, shy guy that I am, I never do. Of course, most women wouldn't encourage a complete stranger who could be a stalker, or worse. So how are my coworkers getting all these dates?

--Lonely Saturday Nights

Oh, come on. Like a woman in the withering fluorescent light of the supermarket is really going to scream, “Help, help, rapist in aisle four!” because you've interrupted her study of the number of carbs in a pack of Snackwells. The real problem is your shyness, compounded by your refusal to lift so much as a meek little finger to overcome it. Imagine applying the same approach to the automotive issues in your life. Maybe your mechanic says you need new brakes. What do you do, sigh “Perhaps I just won't stop”?

Like too many date-starved men, you probably blame your lot in life on what a nice guy you are: “Waah, waah, why do the jerks get all the girls!?” Um, because they march on over and ask them out – as opposed to ducking behind a Ring Dings display and pondering the grain in the cardboard until the coast is clear. These guys treat the bird-dog phase of dating like a giant casting call, methodically hitting on woman after woman until they get to yes. Whenever a woman gives them a cold stare instead of her phone number, they're already too busy looking for their next target to sit around fretting whether icy-mama is married, gay, or thinks they're a walking carbuncle.

You, on the other hand, turn to paste at the mere thought of approaching a potential date; probably because you picture a stern judge sitting on high, asking the woman, “Madam foreperson, your verdict?” “Your Honor, in the matter of the guy hitting on me in the grocery store, we the jury of all womankind find him to be a giant sac of pus.” The problem here is your expectation that women should function as validation-dispensing centers. Hint: It's called “SELF-esteem” not “What Pretty Women Think Of Me Esteem.”

Chatting up a woman is like crashing a party. Act as if you belong, and you might escape getting drop-kicked to the Rottweilers. That said, unless people commonly address you as “Hey, Supreme Being,” why worry that you'll come off as oafish and say something stupid? It's the human condition. You might even use it to your advantage, a la Hugh Grant in his typical onscreen persona; i.e., “I'm completely bumbling and shy, and normally, I would never approach a woman in frozen foods (not even in the potato chips aisle)...but in your case, I had to say something.”

Your assignment? Get in touch with your spine (it isn't just Tupperware for spinal fluid anymore!), glue some hair on your chest, and embarrass your way to a better life. Make yourself make moves on 20 women every week – until the prospect becomes more tedious than terrifying. Don't fixate on the outcome, as this tends to cause lockjaw midway through “hello.” Your goal should simply be having fun. When a woman doesn't seem up to the task, take it as a sign – a big, flashing arrow pointed at the woman behind her, and away from your previously scheduled lifetime of Saturday nights lying quietly on your couch impersonating mold.