Last night my mom and I went out for dinner. Our waitress happened to be an attractive blonde who tried to up-sell us on the happy hour menu. If she hadn’t been so cute, I might have passed because I’m not keen on getting buzzed with my mom at dinner. Instead, I opted for sangria.

We had to ask for our checks right away when the food arrived because we had to catch a movie.

“What are you seeing?” the waitress asked. When we told her, she said she was supposed to see it last night, but her date couldn’t get into it - “he was too touchy and talkative,” she laughed, and here she touched my shoulder - so they left to go to a bar. I noticed she wasn’t wearing a ring when she touched me and the way she said “date” indicated detachment.

My mom paid the tab, but I was left to calculate the tip. I considered leaving my number on the check, but that felt weird with my mom sitting across from me and who knew what this waitress was thinking. She was definitely a few years older than me.

After the movie, I thought about her and the what-if. We meet people somewhat frequently in life for fleeting seconds that leave a mark and whom we possibly never see again. What if some of them are the meant-to-be’s in proverbially parallel lives? What if, on another planet, I did leave my number and I was the guy to take the waitress back to that movie and we were touchy and talkative after the movie?

When are we supposed to jump the barrier and make the passing more permanent?

Maybe I’m a coward and a lot more people do jump the barrier, but I also get too often caught up in etiquette and perceptions. I’m often afraid to impose or over-read signals. Though you could also accuse me of under-reading a lot in hindsight.

What both breaks my heart and inspires me is all the untold, never-to-be romances that pass us by. One of my favorite novels and movies is “Atonement.” What strikes me so much about the film is the tragedy, which only exists in the vacuum of what-if. I don’t want to give away too much if there are any future readers reading this, but the story is centered on a reality and then a fictional after-effect that underlines the tragedy of the reality.

Hopefully some of that made sense.

My last night in Madrid this year, I met a woman on a walking tour who was also very attractive (that’s the catch with all these what-if romances; there’s usually a physical component) and who seemed to take to me to, if she was a bit uppity. The tour ended at 9 PM, my flight took off at 8 AM, and I still needed to get to my Airbnb to drop off my stuff - in case this woman didn’t take me in for the night, you know.

Inevitably, we said bye (or, rather, adios) and wished ourselves the best on our respective journeys.

I don’t even remember her name, and she exists mostly as a shadow of Madrid in my mind, but it’s intoxicating to dwell on some dramatic thread where we fell passionately into something on my last night in Spain and began a whirlwind affair that took me back and forth from the States to Israel (where she lived).

I’ve also imagined scenarios here in Richmond with people I’ve met in passing. It’s no mystery that my time in Richmond seems to be wrapping up, so I have projected romances with passersby where I partially sacrifice my future to fly back and forth from wherever to Richmond or we move away together, which always seems far more idealistic in fantasy than practicality. Most of these fantasies indeed end with a tearful fracture because I need to go do me.

In fact, the what-if scenarios that present themselves closer to home are the sneakiest. Oftentimes I don’t view them as what-if projected tragedies because they’re actual possibilities in the sense of time and space. But I rarely act on them. I envision a tapestry without lifting a paintbrush. Dreamers create their own nightmares, as they say (or so I just wrote).

My biggest curiosity is if others create and retain these romantic dreamscapes with projected lovers and full-circle timelines - and who chases the rainbow to the pot of gold that’s probably not there.

And if anyone knows Amanda who works at the Green Onion in Norfolk, I’d be down to give her my number. And maybe see that movie.

If you liked this, then you may also enjoy:

Survival of the Singlest: Dating In Your 20s

A Dream of Happily Ever After

I Won an At-Home Massage, and Here's How It Went