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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.

Posted by aalkon at April 14, 2006 6:52 AM

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Regrets Galore writes:

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?

Obviously, I didn't read his letter to you before you got to it and did the appropriate editing for your column. But I'm not understanding why he would even WANT a girl who would go back to her cheating boyfriend. Now, technically, the letter doesn't specifically say that they actually broke up, but isn't infidelity the biggest deal-ender in relationships? Obviously, she was devastated by it, so shouldn't that be her cue to give this loser his walking papers?

Now maybe the two of them wrote to Dear Abby and she gave her sagacious and oft-used directive to "seek counseling" occassionally with the addendum, "if he won't go with you, go alone." And maybe, during couseling, he went through an epiphany of operatic proportions and realized how wrong he was to cheat on her, and penitently spread rose petals in her path wherever she went for an entire year...

But barring this possibility, I really can't see why anyone would want someone so pathetic as to go back to the person who cheated on them?

But then again, perhaps they were made for each other. She's almost as big a wuss as he is. I say "almost," because she at least had the courage to "express interest."

Posted by: Patrick at April 14, 2006 9:00 PM

I'm embarassed to admit it, but I know how the letter-writer feels. One day I met an awesome woman, whom I did not pursue out of a combination of spinelessness and pragmatism. (I was terrible at recognizing signs of interest, and due to move cross-country within a few months.)

After the move didn't work out and I returned, I too had regrets galore -- what if she was "the one"? Puke puke, but that's the way I once thought. I arranged a date and... well, things just weren't the same. We were still very fond of each other, but there was clearly no more romantic potential.

This was after barely a year had passed, the woman was still living in the same area, and was not involved with anyone else. How much do people change over seven years? Especially between the ages of 23 and 30? After this much time, Regrets Galore has no right to pass judgment on what this man did while Cameron Crowe was doing principal photography on "Almost Famous".

My message to Regrets Galore, if he's reading: I've been in your shoes, buddy, and I speak from experience that there's nothing to be gained here. At best, you'll learn what you already know; that there's nothing to be rekindled. At worst, you'll be an obstacle in a relationship you have no business being involved in, or you'll be mocked for trying to revive something that's about as current than Monica Lewinsky jokes.

If you care for this woman, do her a greater service by letting her get on with her life. Because she gave up on you a long time ago.

This story can still have a happy ending, but only if you learn from the experience. Nothing cures What Might Have Been like a healthy dose of What Might Be Tonight. Take Amy's advice and go find someone whose window of opportunity is still open.

Posted by: Gary at April 18, 2006 6:13 PM

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