Money on Your Mind: Who Should Pick up the Tab?

Q: I am an financially secure woman in my late 30’s dating a great guy who is also financially secure. We started out as friends without expectations, which is why I think we have so much fun. In the beginning of our friendship when we would go eat I offered to pay for mine and he accepted. I had never had that happen before and at a later time we talked about it. He has been financially responsible for his mother and I feel I am being tested. Now that we are getting more serious I am becoming uncomfortable with this ‘Dutch idea’. Money is the topic but for me the real issue is I miss the special feeling that comes when the guy pays for dinner. How do I address this?

A: It’s good to be frank with your friend. If you don’t tell him how you feel now it’s very possible that you will grow resentful and as a result the relationship will most likely deteriorate.


  1. Lilli

    Instead of splitting each date why don’t you alternate? That way you sometimes have that special feeling of him paying for dinner that you are after, and he doesn’t feel like you’re expecting to be a kept woman. Eventually, if it gets serious enough, it’s all the same money anyways.

  2. Karen

    This works very well with my SO and I: we are unmarried, he is a much higher earner than me but we both have to budget our nights out carefully. Whoever invites pays and gets to choose the activity/restaurant, so there’s no undue financial pressure and each of us is happy to be treated/enjoying an activity of our choice with the person who makes us happiest.

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