A Lovely writes:

My boyfriend and I have always split the bills everywhere we go. One week he will pay for our dinner out, the next week I will. However, recently I have had some unexpected bills that I need to pay off and he told me he would pay for all of our outings until I was more financially secure. BUT every time we do go out, he complains that he has to pay. Should I just pay even though I can’t afford it? What would you do in this situation?

This sounds like one of those “oops, did someone just take me up on my insincere offer?” scenarios. Like when you’re at a bar and politely say you’ll  buy a friend’s drink, but don’t really expect them to take you up on it. And then you get slightly dismayed when they say yes. Which is why I’ve learned to only offer favors when I truly mean it, and your boyfriend should too. Next time he complains about picking up the tab, politely remind him of his offer. And then make it clear that if he doesn’t want to pay, he can (and should) tell you.

If it really is an issue for him, or if he says it isn’t but still acts resentful, then come up with cheaper date ideas. Cook dinner at home, rent a movie or go to the park. Doing so will also enable you to sometimes foot the bill.

If he does want to continue going out and paying, find small ways to chip in (and tell him he has to stop complaining!). Cover the tip at the restaurant, or offer to drive and use your gas. While it’s admirable that he (maybe?) wants to help out, just a little spending on your part will show lots of appreciation.

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