Just because he wants a pre-nup, doesn’t mean he’s loaded. He just wants to keep whatever he has. Sounds like he’s pretty stingy all around is my initial take. Also sounds like he’s has some history with women using him.
I haven’t dated in 12 years so I’m hardly an expert with being ‘out there’. When I was younger, I was more impressed with a ‘nice’ date or even what car I was picked up in. Now, I wouldn’t care because it’s all superficial. As long as I was enjoying myself on the date and connecting with the man, I wouldn’t care how much $$ was being thrown around.
I think you should have been more specific with your request since it doesn’t seem like you wanted anything unreasonable. He might have been put off by you saying ‘really nice date’ which could have meant to him that so far your dates have been ‘really NOT nice’. Why not just say, ‘I’d love it if we could go to XYZ’?
I guess I’m old-fashioned because I never paid $$ on a date. Well that’s not true, I did one time. I went to the movies with this guy and he wanted to go dutch. So I paid for my ticket and saw the movie I wanted to see without him, LOL!!
