40, single, can't get past the first date. "Don't feel the spark/connection" etc. Things aren't about to get easier. Below-avg attractiveness but not horrible, tall, in-shape. Nerdy hobbies. (Think engineering etc, vice DnD). Would pay $$$ to solve this.

Things will get easier women after 40 are less selective.

You can pay $$$ to solve it. They say it's the world's oldest profession (or p2p business if you prefer).

You don't feel the spark, or they don't?

Sample size issue?

They. Probably a "someone better is one swipe away" (?) issue.

> complex situations where you've tried multiple approaches but nothing quite clicks

What are the multiple approaches you've tried?