Dating Someone With More Money

Group Therapy: Dating Outside of Your Tax Bracket

This question comes from Group Therapy in our TrèsSugar Community. Add your advice in the comments!
I have recently been on a few dates with a guy who is fantastic! Our first date was nonstop conversation for four hours about everything and anything. I'm a rather shy person at first so it is incredible that I have been able to open up to this guy so readily. He has been the textbook definition of awesome so far. The only problem is that he comes from old money. I am rather middle class and have no clue how to fit into his world.

He doesn't flaunt his money at all, only contextual clues have led me to believe he is wealthy. I'm fresh out of college and struggling to have ends meet. In my past relationships I've always paid for the majority of our activities, and while it may have annoyed me at times I actually enjoyed paying for things and deciding what to do. If I can't afford to do something I simply don't do it. It's empowering. So when he wants to take me to a fancy restaurant, where I need to Google the etiquette for multiple utensil use, I freak out because I know I won't be able to afford dinner there. I never want to expect him to pay, although he has every time. He is also the type of guy who seems slightly offended by me suggesting I pick up the tab every once in a while. It feels strange because every Disney movie has told little girls this is the prince who will save you, but I feel intimidated by his ability to afford nicer things. I always expected I'd be the breadwinner in the relationship. How do I repay him or get over this? What does a girl do here?

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