Does It Hurt To Ask?

I had forgotten how long it was possible for a teenage boy to obsess on the vagaries of dating. Specifically, I have stood in wonder as I have borne witness to the struggle my son is waging against the forces of the high school social order in hopes of securing a date for the upcoming Winter Dance. He has fired endless salvos of text messages, as well as direct frontal assaults after class and at lunch. Still, she won't budge. He stands on the precipice of her ambivalence: "I'm not sure," she replies.
My wife and I have suggested that he could see if a bunch of his friends all wanted to go together, you know, as friends. But I have memory of the ancient history that is my own campaign to avoid going stag to a dance myself. If you showed up alone, or with your best pal, you had surrendered. You might as well have taken out a full page ad in the school newspaper trumpeting, "I don't have a date for the Winter Dance, and I don't expect to have one for the Spring Dance either." My old man experience tells me that this is far from a death sentence, and at the very least it would free one from the intense pressure of trying to get that special someone to acquiesce to the demands of going to a gymnasium and standing around for a few hours in the most uncomfortable way imaginable. And if you pay an additional twenty bucks, you can get a souvenir photo of this most memorable evening that you can cherish forever.
After going oh-for-five in my sophomore year, I managed to swing a date to the Homecoming dance with a cheerleader. As a point of clarification, she had only recently made the leap from being a flag girl in band to the upper strata of our caste system. I knew her when she was "just a flag girl." After the exquisite torment that was that evening, I spent the rest of the year chasing after that same girl, never fully comprehending that "I'll think about it," may have been the most polite way she could have responded to my tenacity.
In my senior year, I had it figured out, and after a mutually awkward Homecoming dance that year that turned out to be a mildly entertaining pas de deux between two people who probably wanted to be there with someone else, but I had a nice time. I missed the Christmas Dance that year, but by January I had secured the Holy Grail: A Girlfriend. I had a date for the rest of the social events of the year, and since she was a junior, I was assured a victory lap the following year, if I weren't too busy at college.
Well, as it turns out, I took a year off after I got out of high school and that meant I was available for every dance that year, as I struggled to maintain the relationship that would allow me to go to every dance that year. Was it worth it? Of course it was. I was living the dream, after all. The dream that burns deep inside my son's heart. I have tried to share some of my worldly experience with him, giving him suggestions of strategy and alternatives to the tireless texting and begging. His reply? "I'll think about it."