Question to those who used to be older singles

Simply put, things just clicked. I didn’t analyze it the way you are trying to do. I was 35 when I got married, and when I met my wife, we just shared things in common, has easy conversation and she had a beautiful smile (and still does). I didn’t ever have a checklist but I did want someone who was interesting to talk to and shared similar hashkafa views as well as secular views on things like money, etc. In the end, follow your heart if basics in hashkafa are in sync

My parents got married at an “older” age (at the least, significantly older than they’d’ve wanted, which is the standard by which I judge these things these days). While neither of them have ever given me systematic answers to all of your questions, one interesting thing which my mom mentioned once is that there were several opportunities over the years for my parents to have met/been introduced, but because of different priorities which my mom had when she was younger, which mellowed naturally (not because she’d “settled” or “readjusted her expectations” due to shidduchim), had she gone out with my dad seven years earlier she would probably not have married him. The fact is, people’s priorities and characters do change naturally over time, and forcing them to artificially hold themselves to a set of arbitrary societal standards can be foolish. (That wasn’t the specific case with my parents, but I’ve still seen it in action among others.)