05/12/2015 02:34 pm ET Updated May 12, 2016

Trying to Reason With Prom Season

When my son pitched a two-hitter and knocked in the winning run, I cheered. When he got into the college of his choice, I hugged him. When he won the English Student Of the Year Award, I shrieked. Still, it all pales in comparison with my reaction to when he said he had a date for his school's senior prom.

For the longest time, he wasn't going to go. Then, he decided he'd go dateless. And four days before the event, he texted to say he'd be attending with a girl. From that moment, I became a suit searching, corsage buying, Uber ordering machine. I spent more money on his prom in less than a week than I did in six months planning my own wedding.

I've seen Carrie and Back to the Future. I know how important a successful prom night can be for a young person's mental and emotional development. It's the first time boys are expected to dress like men, act like gentlemen and make out like studs. It's the last chance for high school love stories you can exaggerate the hell out of years later.

However, much of my enthusiasm came from a pretty selfish place. We grow up hoping not to become our parents but, at least where prom was concerned, I was hoping my boy wouldn't grow up to be me. When it was my turn to go a few decades earlier, I was shot down by each of the five girls I asked. I spent prom evening looking out my bedroom window, watching well-dressed classmates pose in their driveways for pictures and then curling up with The Love Boat and Fantasy Island. That specter has haunted me ever since, second only to the ghosts of multiple failed attempts at climbing rope in gym class.

I like to think I've never been that helicopter parent buzzing over ever move his kid makes, trying to relive his life through that of his children. Before every baseball game he's ever played, I made sure to not build the event up too much. During all the Saturday nights he spent at home with me instead of out with friends, I'd promise that college was where he'd blossom socially.

Then, prom season came along and I'd watch enviously as friends posted Facebook pictures of their children with their prom dates. My pursuit of his prom experience got so bad, my questions for him about going outnumbered my questions about his homework by about 10 to one. Every conversation I tried to initiate about his plans for the event was eventually greeted with a sigh and an eye roll. My obsession with what should be his fun evening of firsts was making it more on par with chores like cleaning up after the dog.

That's when I got Shiela's Facebook message. It had been 38 years since we'd last spoken. I'd met her when I started working at a nursing home after my freshman year in college. She was a nurse's assistant. I was the kitchen help. I'd never even held a girl's hand before. She actually talked to me. It was the perfect match, and we dated for a few weeks. Right up until I learned she was marrying somebody else.

I coped with the loss of my first date/girlfriend/sexual endeavor by enjoying my first romantic rejection blackout drunk. The last time I saw her, she was depositing me on my parents' doorstep after finding me on hers at 4:00 a.m with an empty 12-pack of malt liquor. Hence, my excitement at seeing her name in my Facebook inbox. Just as my son was getting ready for his first big evening of firsts, I was hearing from the woman responsible for so many of mine.

She asked if I was the same Craig Tomashoff who used to live in the Seattle area many decades ago. I shot her back a note explaining that I was, and that if I remembered correctly, she and I went out for a while. I was certain she'd kept up with my writing all these years and couldn't stop regretting our breakup. Then, I got her response. She had recognized my name, but couldn't place me.... was I the guy who was into photography? I explained I was not, she wished me well and that was it. We will never e-speak again.

They say you always remember your first but, based on Shiela's brief Facebook check-in, that doesn't necessarily apply to your partner's memory. She moved on years ago. Meanwhile, I'd wasted decades replaying the experience in my head, like a movie whose ending I kept hoping would become a thrilling, Spielberg-ian spectacular but instead would forever be an M. Night Shyamalan-esque letdown.

I was using my son's prom night as my chance to create my own sequel: kick off his love life with a story far more memorable than mine. As I drove him to his date's house (from which they'd Uber the night away), I had planned on throwing in a daytime talk show's worth of dating advice. As it turns out, judging by his nervous staring out the window, literally the last thing teen boys want is their dad advising them on the proper lip suction for kissing a girl goodnight.

So I escorted him to his date's door, met her mother and took a couple of pictures of the hopefully-soon-to-be-happy couple. Then, I turned around and drove home to think about anything but prom. Memories would make themselves just fine without any help from me. Or they wouldn't, as my Shiela encounter clearly demonstrated. Being in the moment is all that counts, and my son needed to get out and just let loose. For the first time, I realized I had to let him have his own personal life. And this was a first time I will definitely have to remember.