I put a social worker through grad school. Her entire family were Freudian psychoanalysts. Every Friday we'd go over to their house and violate HIPAA as they shot the shit about patients, therapy, and how you mindfuck people for money. She was also an emotional sadist; her jollies came from tweaking you when you were up so you would be down, and tweaking you when you were down so you'd be despondent. Once despondent you were reliant and once reliant she could crush you some more. Four years of that and you learn some things about emotions and human nature.
I bring this up because "introspection" plus "training" leaves you with "holy shit I coulda dated so many more girls in high school."
You gotta let it go, man. Mathematically? You're with that girl somewhere in time. Enjoy the hypothetical and enjoy the reality.
Li'l story. I built a car from the framerails up. I drove it from New Mexico to Washington, on my own, tweaking it as I went, breaking in the engine, discovering the auxiliary tank leaked and that I'd probably blown a head gasket because my cooling setup was, not to put too fine a point on it, designed by a seventeen-year-old. And somewhere north of Salt Lake and south of Boise I ripped past a girl with her thumb up and didn't even slow down.
Because, you see, if I broke down where would she be?
It took about a year for me to realize that if I'd broken down she'd be on the side of the road, exactly where she was then. Over the course of that year she'd become The Most Beautiful Girl In The World and also My Soulmate. There she stood, thumb perpetually up, for a good ten years at least. She even made it into a screenplay (that was a finalist for a fellowship I might add).
About Year 11 I realized I was obsessed with a glimpse at 80mph of someone who was more likely than not a drug addict or runaway or otherwise damaged human (I had a real thing for damaged humans) and that whatever romanticism I assigned to the outcome had nothing to do with anyone but me. It was liberating.
But there's an alternate universe where I picked her up. There's an alternate universe where we're married, there's an alternate universe where she's a serial killer.
Charlie Kauffman is a loser. Anyone who can take a story like The Orchid Thief and make it about themselves is bereft of insight. Find something other than sour grapes to chew on. You'll thank me.