[ExtraRoulette]

I get the optimization thing. I also replay situations in my head and how it could have gone better. I even save notes/reminders/mindmaps for the next time I talk to someone or I'm in a particular social situation. That's just how my mind works, and I can't remember everything.

I also second your approach. I have a todo.txt file of various restaurants, experiences, places my gf wants to visit. Next time I want to plan a date, I look up the list ("Hey babe, let's go that that [RESTAURANT MENTIONED 3 MONTHS AGO] tonight. It's proven to be a very good system. <3