The problem with stuff like this is that everyone wants different things. This lady was great, did what she ought to. But this guy wasn't looking for an absolute catch, he was looking for an ego boost with low effort.

His first issue screams insecurity in his appearance, and that's fair, a lot of people have that issue. But rather than telling his date not to dress nicely, he could be putting effort into his appearance. A nice haircut and some decent quality, well fitting clothes that complement his body could go so fucking far.

The money issue though, that requires decoupling from the mindset of his role being to provide. It may be difficult, especially if he has little understanding of what he actually provides in a relationship (or what he could provide) beyond money, but it's valuable mental work to do. People don't stay in love with you because you pay the bills, they do it because they enjoy your company and feel you're working together through life.

All this is of course moot by him claiming she's the lucky one, at which point, yeah fucking yikes dude