at the very least, he'd be super impressed that she got into it so young! he was 30 before he even worked up the guts to start working toward his own place in any form. i would definitely love to round out his awkward dating history, though! her personality actually sounds like they'd normally get along well, but the combination of him being weird about the possibility of dating younger girls all of a sudden and just being super fucking anxious about being single again would easily have made it gone badly. plus, if there's a local business association or something, they can now feel super awkward at the occasional meeting.