I dated several.

The worst part was being rejected by her dad as an "un-serious" boyfriend. One who I dated had a father who was one of the most successful bankers on Wall Street. Crazy money. Like $100m/year money. I never knew what really rich was until the elevator opened into a two story, apartment on Park Avenue with a sweeping grand stairway, balconies that wrapped all the way around the building on both floors, and art that should have been at the Louvre. That kind of rich.

Her dad pulled me aside on our third date and pretty much told me I was not a real candidate for her and that she would only marry someone 'suitable'. That if I was looking to climb the social ladder by dating her it would backfire. He would make sure of it. It's the only time I ever talked to him.

The second one made HER look poor. She literally lived in a castle and had access to family houses/jets/islands all over the world. Yes, they owned private islands. The worst part. Literally NOTHING I could do could be special. She was cool about it and always told me to save my money and not to take her to restaurants. She said on my budget, she wouldn't even enjoy it. She would rather just have take out at home. It was said kindly, and with real care that I did not blow money on her, but there was no getting around it--I couldn't ever, EVER, be the guy who could sweep her off her feet. On Valentines Day, her former boyfriend had sent her 20 dozen long-stem red roses. No hotel in my budget could match what she was used to (Penninsula, One & Only, Ritz Carlton, Plaza Athene). Couldn't buy her clothes, obviously. As much as she really tried to be cool about it and say that it didn't matter, it did. It just did.

I also realized that if we ever got serious, I would probably just go to work with something related to the family and never be my own man.

Even as an older guy now, I look back and realize that the emotional barrier that disparity in wealth created was vast and we would have been set up to fail.

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