I'm from NYC. Dated two girls who were well off.

One wasn't SUPER RICH, but definitely well off. But it was still weird to me because I grew up really poor. She mentioned it but I didn't see it until I went to her house in North Carolina for Thanksgiving. You literally needed to DRIVE around her estate. She grew up in a 20-room mansion. Pretty sure it was a plantation and they owned slaves at some point or something judging by the house. Her family wasn't snooty or anything but... the whole atmosphere just felt weird. I just felt like this wasn't somewhere I didn't belong. My girlfriend and her family were totally fine and nice people. I just personally felt completely out of place.

Also, she attends a lot of fancy events, like charity balls and galas and gets invited to all these ballet fundraisers and stuff. And as her boyfriend, I had to go to these things. I hated every minute of it. It was helpful though because in the beginning, I honestly didn't even know how to eat properly at fancy meals, all the etiquette and shit. So I learned a lot there.

Now, the other girlfriend was SUPER FUCKING RICH. She was a trust fund baby and her parents were real estate developers in NY and China. She literally rotated between 4-5 apartments in NYC, had a huge loft in SoHo, a condo by Central Park, a penthouse by Columbus Circle, a townhouse on the UWS, etc. We dated very briefly, maybe a month, but I already couldn't handle her. She had zero interest in school or pursuing any career. I mean.. I don't blame her. She went to classes and stuff but she just had zero idea what she wanted to do. And similar to the other girl, she went to VERY upscale places and I couldn't even bear to look at the menu because I couldn't even bring myself to order a $250 dinner... She paid for everything and I just felt really weird about it.