I've tried all that. I've picked out a couple places for us to go. He agreed and saw that is was busy and kept driving. He said he would feel too claustrophobic.

Another time he picked a place but it was closed for a private event. So I picked a place and he got almost angry about it (angry for him, he doesn't really get mad). He said they wouldn't even let us through the doors because we're clearly not rich. It definitely wasn't anywhere close to that upscale. It was a solidly middle class cafe and bar. He will only go to shady hole in the wall places. That can be fun, but not ALL the time.

I guess I can try going some place by myself, but I'm not sure where. I feel like getting dressed up and going to a bar or a cafe alone is just going to seem like an invitation for guys to talk to me.