I have mastered the art of overthinking a coffee date. My friend still teases me about the spreadsheet I made for lunch locations. It is a strange skill to have, really.
Honestly, I get it completely. My brain does the same thing, running through every single option until I'm paralyzed. Here's what finally worked for me. I force myself to pick just two solid choices, then I literally flip a coin. It sounds silly, but it stops the endless loop. The goal is just to go and connect, not to find the perfect spot.