Let’s get real: He foots the bill all the time and isn’t happy about it

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First Posted: 1/4/2015

Dear Melissa,

I am seeing a wonderful woman who is pretty much everything I was looking for in a mate. Things have been more than perfect, but through the dating process we go to out to dinner roughly four times a week. My minor gripe is that not once has she offered to pay for a meal. I am afraid that she is just expecting me to pay for everything all of the time and while I make a comfortable living, it has certainly taken a financial toll on how I have budgeted my life. I am not cheap by any means, I just want to have her offer on occasion.

Other than this, she’s great and I’m happy we’re together. Am I being petty and overly sensitive? How should I approach this without jeopardizing everything else?

Forever Footing the Bill

Dear Bill,

It seems like she might be taking advantage of your generosity. As a girl who has gone on my fair share of dates, I try to at least offer money toward the check or the tip because it makes me uncomfortable to have someone constantly supporting me. It seems like this girl is used to being “kept” and that could be a red flag for troubles ahead. Try cutting back on the number of dinner dates and offer to stay in. Or perhaps next time you are out casually bring up in conversation that you spent more than $100 dining out that week. Maybe she will get the hint. If she doesn’t, try doing different things on dates that aren’t such a financial burden. Some of my favorite date nights are spent taking a walk under the stars or curling up on the couch with Netflix and a big bowl of popcorn and a bottle of wine. Hope this helps!