Feeling split: When my girlfriend and I started dating, I noticed that she never reached for the check when at dinner, bars, etc. I found this unusual because in my previous relationships, my partner and I would split every check. When I asked my girlfriend why she didn’t pay, she said because of the damage men had done to the world (through rape culture, violence against women, the wage gap, “boys clubs,” and the patriarchy in general), I should pay for her. She didn’t use the word “reparations” but that is essentially what she was saying.

I understand her point at a macro level. However, from a day-to-day standpoint, though I earn more than her currently, she comes from a wealthy family who subsidizes her lifestyle, while I am actually sending money back home to my parents. She went to private school, I went to public school. It seems to me that from an “intersectional” lens, we both have some sort of privilege.

I also don’t understand why this issue in particular is so salient. I asked her if she paid for her Black friends because of the structural racism Black people face and the corresponding wealth/wage gap, and she said that “didn’t feel as personal to her.”

We are at an impasse here. How should this be addressed?

A: Dating is a time for noticing when you’re at an impasse and decide not to get more serious. It is not a time for insisting that every difference and personality conflict must be resolved. Here, you’ve learned that you and your girlfriend don’t share values about who should pay on dates. But more than that, you now know that she’s not interested in being a team player when it comes to expenses—even though she’s wealthier than you are—and either doesn’t care much about structural racism, or only cares about structural issues that provide a basis for her to do whatever she wants. Do these things make you like her a bit less and feel a bit less compatible with her? Ask yourself that, rather than trying to figure out how to change her.

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He knows just enough feminist lingo to almost pass for one, but he's still salty about actually having to pay for dates, which means he's a cheapskate. The jab about paying for black friends is such a straw-man argument, and makes him look petty as hell. Thoughts?