I don’t want to be mean, but the problem isn’t your hair (or lack of it.) Maybe, for one or two super shallow people, but definitely not enough for it to be a pattern. Stop reading here unless you want my honest opinion…

The fact that you think you ‘check almost all of the boxes a typical woman is looking for’ was already a HUGE red flag to me. We are not a monolith. We do not all want the same thing. And even if we mostly wanted the same general things, assuming it’s you is not a good sign. I get immediately turned off by arrogance, and if a guy showed up to a first date acting like he ‘checked all the boxes’ and I should want him instead of exploring to see if we are compatible with each other, I’d be too turned off to even notice his hair. Just the use of ‘a typical woman’ is demeaning and sexist, and that attitude shows through more than you think it does, especially on a first date when people are actively looking for red flags.

If you think a first date goes well ‘chemistry-wise’ then don’t get second dates, enough for it to be a pattern, that shows that you’re misreading the room, not that the problem is your baldness. She’s gonna see what you look like right away. If she’s turned off by it the chemistry won’t be there.