Dear Trophy Wife In Training,
How do I get my rich boyfriend to treat me right?
I (F, 24) have been dating my boyfriend (M, 27) for a little over 8 months and he refuses to spend any money on me.
After every date, he venmos me for my half. Even for stuff as cheap as a $2 ice-cream cone. As for gifts? Forget about it. Nothing. Not even a cheap card for Valentine’s Day. He once even won a teddy bear at a carnival but reclaimed it at the end of the trip because “it was really his because he paid for the games.”
Here’s the thing though, he’s actually super wealthy! He works a high paying finance job (a little shy of $200k/year) and he also comes from family money! He has no student loans and is clearly very financially stable. I also work in finance, but more on the sales side so I’m only making around $60k a year, plus I still have some student loans I’m paying off. I’m not as well off as him, but I make my own money and am clearly an “independent enough” woman.
So, I don’t get it? Why won’t he spend any money on HIS GIRLFRIEND!! I’m not a gold digger! I don’t mind paying for some things, but this is just getting ridiculous! How do I prove I’m not a gold digger, but also get him to pay for at least some dates?
Sincerely,
I’M NOT A GOLD DIGGER!!
PS: I know your account doesn’t really focus on how to date rich men, but I was just hoping you would be able to give me a LITTLE guidance about my situation.
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Dear Aspiring Gold Digger,
Dump him.
Full disclosure: I fully understand you’re not a gold digger. If you were, you’re terrible at it and need to rethink your dating strategy.
However, I will point out you are actively swept away with a dream vision of your life with him. You see his professional achievements (and have likely seen some of the family assets – perhaps a lovely beach house?) and are smitten by the idea of dating your own up-and-coming JFK. A semi-charmed life and nothing wrong with wanting that.
However, the reality is he’s being cheap and continuously demonstrating he does not see you as a part of his life worth investing in. While paying the bill isn’t the ONLY way a man can show he is invested in your relationship… it’s a pretty good indicator.
Quite frankly, you would be better off dating a guy with less net worth who will at least spend $2 on you. I know your email is not a full reflection of the relationship, but I URGE yourself to evaluate what exactly you like about him. As I said previously, you’re likely in love with the IDEA of him (along with the future you can picture with him).
The reality is, you need to dump him. You deserve chocolates and roses on Valentines day. You deserve a man who feels pride in winning you a carnival toy. Finally, you deserve a man who sees you as someone worth investing in. You deserve better.
Stop being some loser’s placeholder girlfriend, and start being a better man’s dream girl.
Love,
Trophy Wife in Training
Posted with permission

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