Not comfortable accepting handouts from wealthy boyfriend

Dear Carolyn:

I’m a college student dating a very nice guy who happens to come from a wealthy family. I really like him, we get along great, we each contribute equally to the relationship, and we see eye-to-eye on many things.

However, the financial differences between us have begun to take a toll on me. It is difficult for me to keep up with him and his friends — who have become mine — when it comes to eating out, going to concerts, Ubering long-distances to bars, etc. I have addressed my financial situation with him bluntly in the past, and he offers to pay for me constantly.

I feel guilty for the normal reasons, but also because his money is really his parents’ money, and I feel weird adding expenses to the credit card bill they pay off. This weighs much more heavily on me than it does on him, despite my subtle offers to cook at home or to not drink and be designated driver so I can drive instead of paying for rides.

Is there a different approach to take that would save my wallet? Do I accept his offers to pay? Or is this a wedge in my social life that must be accepted?

— Anonymous

There’s an approach that would save you aggravation, shame, awkwardness, misunderstandings, and the toting around of weird-heavy feelings in general, not just for this one issue: saying what you mean.

You said you “addressed my financial situation with him bluntly,” which is great — but in the present you’ve gone “subtle” when putting the theory of your finances into practice.

There’s a time for subtlety, but this isn’t it:

“I know I’ve told you I’m not wealthy. It means I can’t afford places you and your friends can — but I am also not comfortable with someone always paying my way. I take pride in taking care of myself. So I’d like to do more things together that I can afford. And when I volunteer to drive, please let me drive.”

Or make other suggestions that would help you feel better.

Make it clear that his spending more won’t always fix it; sometimes he’ll have to spend less. It’s a complicated problem that asks both of you to draw on your senses of self — and on your feelings for each other — and then to figure out what you’re comfortable with and why.

Assuming the whole process doesn’t break you up, each of you needs to give up a little something for the other without compromising yourselves. Will he skip the nice dinner out once a week? Twice? Always? Will he ask the friends to do the same? Will he embrace change or roll his eyes all the way to resentment? Will you let him treat you sometimes so he can still enjoy nice things, since he has every right to? Can you reconcile your comfort levels with spending parental money? Will you both be good sports about finding a balance that works?

There isn’t much to celebrate about being broke, but there’s a lot to appreciate about a clear window into your own strengths and your strength together — as demonstrated by your willingness to advocate for yourselves and to meet each other’s needs.

— Washington Post Writers Group

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