'I'm never sure if girls like me or just my wealth'

I come from a well-off family and have been trying to find someone I can get into a serious relationship with for a while now. I have dated a lot of women, but I am never really sure about why they are with me. I am not very good looking, but I have a lot of money and always take them to fancy restaurants. I don't know if they are with me simply because they know how rich I am. I want to find someone who truly cares about me and am always trying to figure out if the person with me is being genuine. This makes it very hard for me to have any long-term relationship because it inevitably makes me doubt everyone. I don't know if I can ever find happiness. What do I do?
I think you're over-thinking this. A lot of seriously rich men and women manage to have successful relationships, which doesn't necessarily mean they are all in marriages of convenience. If you like someone, and someone likes you, shouldn't that be enough for a start? Focus on how you get along with someone, how comfortable you are with opening up to someone and vice versa, how a person behaves in public and private, what a person's principles are. Those are things that matter more, especially when it comes to deciding who you want to spend the rest of your life with. Don't look at everything with cynicism, because down that road lies unhappiness. Also, do keep in mind the possibility that you may find someone richer than you who may have no interest
in you whatsoever.

My boyfriend wants me to pretend that we are not in a relationship when we meet his friends, because he says they won't approve of me. I don't know what he means by that, because he doesn't elaborate. If he's ashamed to be seen with me, why am I in this relationship?
Why indeed? Dump him.