Notes from a Future Old Man

I’ve been at my parents’ place all week, in the house I grew up in, and in my bedroom closet I found a bag of old letters from every girl I “went out with” from roughly the ages of 14 to 18. One was from a girl I had a summer fling with when I was 16 and spent a few weeks in Vermont at a pre-college program. There had been a bit of a love triangle between me, her and another girl, and in her letter, she wrote: “I’m so sorry that more couldn’t have come out of our relationship. I realize how much you also love J*****, and I don’t blame you – she’s great.”

This blew me away. How did I manage to pull that off, whereby I dated two girls in a five-week span, and this was the incredibly mature, selfless attitude one of them had towards the other? I don’t think I’ve even met a female in my adult life who would express this type of sentiment.

Then I started reminiscing about high school. I thought back to my sophomore year girlfriend, and how my best friend dated her for awhile after we broke up – and how there was no animosity about it amongst any of us. How was this possible? What world did I exist in? Were there Oompa-Loompas there too?

In fact, how was it possible to date anybody after I had already been with someone else at the same school? If I was in high school today, as an adult, I would probably just go ahead and change schools rather than deal with the awkwardness of seeing an ex-girlfriend on a daily basis, let alone seeing her after I’d started dating someone new – someone she might even be friends with. But I suppose most of us dated multiple people from the same school, and it just wasn’t a big deal. We all had classes together, projects to collaborate on, dances to attend, and we just dealt with it, I guess. Today, I try to avoid restaurants in the same neighborhood where an ex of mine lived five years ago.

What a simpler time it must have been. When did things get so complex? When did we lose this maturity to be able to say to each other, I’m sorry things didn’t work out, but I can understand what you see in this other person who isn’t me, and I don’t hate you for it?

It’s almost like I want to time travel back to the 90’s and ask my teenage self for dating advice. He had skills. 

He’d probably tell me to go back to watching 90210. Back then, I aspired to be Dylan McKay. Now I aspire to be Larry David. Big difference.