Stalling Head Over Heels

I’m 30 now, but I fell in love with a wonderful girl back when I was 23. After her boyfriend cheated on her, I held her while she cried. Soon afterward, she expressed interest in me, but I couldn’t muster the courage to ask her out due to an embarrassing situation at home (my father’s debt and his health problems). Seven years later, I still can’t let go of what might have been. I just heard she and that same boyfriend recently moved away together, and I'm crushed. Should I contact her just to see how she’s doing?

--Regrets Galore

It’s a good thing other species aren’t evolved enough to be as counterproductive as we are, or the food chain would empty out in about a decade. Come on, do you think a male deer on the make sniffs doe pee on a branch, and says to himself, “Naw, Ma’s been having a bit of the mange lately, I think I’ll take seven-year mating sabbatical”? So, your family tree has a bit of bark rot. Join the club. The essence of being human is being something of a screwup. Everybody’s got problems. Smart people view them as opportunities for growth (see The Consolations of Philosophy by Alain de Botton). Others, such as yourself, prefer to repurpose them into excuses for acting like a wuss: “I can’t ask you out -- it’s too hot, it’s too cold, Daddy’s too poor, Daddy has a goiter named Fred.” Well, unless Fred’ll be joining you on your dates, and Daddy, too, in a wheelchair and leashed to his breathing machine…what’s it to you? Then again, humiliation has excellent entertainment value. Nobody bonds with you over tales of your greatness. People want to hear about how human you are. They want to know about that time you were so poor you had to dress up as a chicken, clucking as you handed flyers to pedestrians; or rather, as you chased pedestrians, trying to hand them flyers so you could get paid before you died of heat exhaustion. There is, however, a difference between serving up a splash of self-deprecation -- suggesting you have confidence to spare -- and inviting others to look on as you drown yourself in a bottomless vat of self-perceived loserhood. Extricating yourself from that vat could take years of therapy and a forest of motivational Post-it Notes -- reminding you not only to replace the refrigerator bulb, but to like yourself intensely while doing it. Or, you could just stuff a set of walnuts in your underwear (the faint clacking will remind you they’re there -- if the discomfort or a band of rabid squirrels doesn’t get you first)…and go out in the world and hit on girls. But wait, what about your One True Love? Sure, you could call her -- now that there’s even less of a chance she’ll impede your slow, lonely march toward incontinence and death. Or, for a change of pace, start asking out other girls like, well, like they’re going out of town to live with their boyfriends. At some point, you’ll learn what players know -- that success in dating is largely a matter of mathematical odds. Ask three girls, you’re likely to get three rejections. Ask 300, and a few are bound to say yes (maybe even a few keepers). In time, you should come to understand that it’s self-worth, not Daddy’s net worth, that matters. Of course, sticking with imaginary relationships is a great way to preserve your own net worth -- considering the low cost of imaginary dates, wedding rings, private schools and college educations.