Keep getting rejected by guys I thought would definitely go for me?

I’m a somewhat attractive woman who is well educated with a decent job and goor personality. In the past two years I’ve put myself out twice and asked out men for coffee who were older than I am and not conventionally attractive. Don’t get me wrong- I found them very attractive but my girlfriends would say “he’s a decade older than you and not that cute. You’re out of his league. You like him?” But I really, really did like both guys. I asked second guy out for dinner under the guise of a meal to discuss careers (we are in related fields), but I flirted hard all night (laughed at his jokes etc). Next day nothing. No follow up text, no “let’s do this again.” Crickets. What gives?

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+1 y
I will say that I ended up being good friends with the first guy I asked out and I jokingly told him I asked him out months later and he rejected me. He acted genuinely shocked and wanted a second chance but I was over it by them
Keep getting rejected by guys I thought would definitely go for me?
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