Dating someone wealthier

(written by lawrence krubner, however indented passages are often quotes). You can contact lawrence at:


I dated a guy once whose father was quite wealthy and worked in finance. He often told me things straight-faced that, I—someone who had grown up on food stamps—found preposterous. He’d say that the couple grand he received as allowance each month was not very much money, and that his family was extremely careful not to show off their wealth too much, which he told me while we sipped booze on his dad’s $80,000 speedboat.

We went to restaurants where a night of dinner, drinks and appetizers easily totaled $300. These were some of the first “nice” places I’d ever been, and I had to quickly learn how to act or dress “correctly” (I’m sure I did not). I ate things I’d never had before growing up on welfare in the South but which to him were absolutely commonplace—ostrich, oysters, expensive steak. I found the way he spent money totally fascinating and yet totally appalling. That is to say, he spent it thoughtlessly, as if he knew it was always coming in a steady stream. Because it was. And as such, he never seemed to truly appreciate what he was eating or consuming; it was simply part of his normal, what he’d grown accustomed to, while these things were exotic to me.

When he moved out of a one-bedroom college apartment, movers had already been ordered and paid for so he wouldn’t have to pack or lift a thing. I had been hauling everything I owned in the back of my shit car to every place I’d ever lived since I turned 18.

While we dated, that car broke down and I could not afford to fix it. In a move that is possibly the most generous anyone has ever been to me, his parents gave me a car—his younger sister’s castoff Dodge Neon—which they’d only even given her as a test car for a year prior to gifting her the new Mustang she really wanted. I needed it far too desperately to turn down out of pride.

The relationship didn’t work out, but it wasn’t because of money. At least, at the time I didn’t think it was. But in retrospect I realize how uncomfortable it had all been for me to be around someone who had it so easy while I struggled so much. There was a dynamic I also came to resent as much as I appreciated it—that of the wealthier person always explaining to me about why some such thing was better than the what I was used to. It was a running joke at one point—this prime rib is just like the one on the buffet at Holiday Inn!—but it left me feeling eternally out of my element. I was attending college, trying to work my way into the middle class, but I only knew about most of these far-flung things because of books, never firsthand experiences.