Dilemma: I am dating this guy who is 36 (I am 40). He loves to hang out BUT the places he likes to frequent make me want to puke..........Applebees, Fridays, the local hood bar. I HATE those places and I don't even go to those places with my girlfriends. The crazy part is that he has money. He is an entrepreneur with at least 3 streams of income, so there is no reason for us to go to these places.
Initially, I picked the places where we would go and he would get "dressed" and end up loving the places but as of late whenever I suggest a place, we get into an argument because he doesn't want to go. He thinks the places are too stuffy (which they are not, at least not to me). The last place we ate was a seafood place near Baltimore (Timbuktu) and upon entering the place, you could smell the carpet and the kitchen....together and it was freezing. He stated that he wanted to show me a good time (which i appreciated), but I was not having fun at all AND the sight of him holding his fork like a caveman was "grinding my gears". All I could think about was going home. Once I got home I sent him a text thanking him for lunch, etc etc etc. But since then, I have not felt compelled to go back out with him again.
When we went to North Carolina he picked the ABSOLUTE worse motel for us to stay in. I almost cried. I asked him if we could please go somewhere else and he said that he got the hotel for me but really wanted to stay at his aunt's house. Again, money wasn't a factor because we were there because he wanted to buy yet another ATV cash.
I don't think he feels comfortable around white collar blacks and white people. He loves the hood (even though he would never live there). He typically dates women with numerous children and (per him) they love whatever he does for them. He told me about a chic that he is dating (30 with 5 children) and that he took her to Sugar and she was so happy to be there.
How do I get him to feel more comfortable going where I want to go???
Because this will soon come to an end if he can't switch it up.