Dear Penny: My Rich Girlfriend Expects a Man to Pay for Everything

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Dear Penny,

I recently ran across your column about the boyfriend who wanted his girlfriend to pay his bills, which was of interest to me. 

I am a middle-aged, currently single man, who has been in a relationship for 10 years with a woman who started as a friend way before that. She is divorced and has no kids at home. She got an inheritance from her parents when they passed that allowed her to retire at 58, pay off her house and become debt-free, while allowing for ample travel, investing, etc. 

To this date, I have no idea how much money she has, (she freaked out the one time I asked) but clearly it was enough to stop working completely. Her dad was a doctor, so I am sure the amount was comfortable.

I am still working in my 60s, which is my choice. No inheritance for me, but I have been able to save a decent amount of money via a 401(k), while still being able to enjoy life as a middle-class person. I have no doubt she has more money socked away due to the inheritance than me, but I dare not ask. 

All that being said, I am in somewhat of a reverse situation in that we also live about an hour away from each other and pretty much have a weekend relationship going on as well. I do 75% of the trips, which is around 150 miles round trip. I also pay for all the meals, outside entertainment, etc. I don't expect her to contribute toward any household bills, and neither does she.

On the other hand, I spend at least $500 per month on us going out to eat, entertainment, etc. She never offers to pay for anything, much less drive us anywhere, even once in a while. She subscribes to the old school, where the man pays for everything. 

In my mind, it's not even a money thing. It's more of the principle — every now and then, offer to treat me. I'm still out there working, being self-sufficient, while she is doing whatever she wants every day.

I'd be curious as to your thoughts on this. I do love being with her, but it sure seems like it is a one-sided partnership.


Dear C.,

A one-sided partnership is still a one-sided partnership, even when it’s couched in old-school values. The idea that one person should pay for everything in a relationship is ridiculous, particularly when you both have financial means. Gender isn’t a factor here.

But your girlfriend isn’t a mindreader. You’ve been paying for everything, driving her around and doing most of the traveling for 10 years. From her perspective, this sounds like a great relationship. How would she know that you’re irked by the fact that you’ve been pulling all the weight if you’ve never brought it up?

Dear Penny

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If you want anything to change, you’re going to have to say something to your girlfriend. You don’t need to make this about how much money each of you has or the fact that you’re still working.

I think you summed it up beautifully for me. You can tell her: “I love spending time with you. This really isn’t about money, but about the principle. Every so often, I’d love it if you could offer to treat me.”

After a decade, she may be surprised by this request. But it’s hard to imagine a reasonable person taking issue, especially since your girlfriend has plenty of money.

If she does object, you’ll need to accept the fact that you’re far more invested in the relationship than she is. What you do with that information is up to you. If you enjoy spending time with her, you can continue things as-is. But do think carefully here: Do you really want to be in a relationship with someone who puts their silly, antiquated values above your feelings?

Even if your girlfriend agrees to give more, she may need a bit of nudging at first. Don’t be afraid to nudge her a bit. It’s entirely appropriate to say “Want to take care of this one?” here and there when the dinner check arrives. If you’ve had a long week, tell your girlfriend that you’re tired but you’d still love to see her if she’s willing to make the drive.

Don’t expect this dynamic to change on its own. But hopefully if you tell your girlfriend what’s on your mind, she’ll do what she can to show that she appreciates you.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to [email protected] or chat with her in The Penny Hoarder Community.