Love Letters: Should Men Pay For Things Most of the Time?

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Dear Meredith,

I have been dating a man I met online for a year now. When I first met him, I thought he was divorced because that's what his profile said. After about two dates he told me that he was still living with his wife, but in separate bedrooms. He also said that they hadn't had a relationship in a while and that she started dating someone about a year prior and had been leaving every night to be with him. He then told me that he had a couple of affairs while they were married. He said he did this because they were no longer physical. I have trust issues and was not sure how to handle this, but I liked him so I ignored it.

When we first met, he paid for everything. After he told me he was finally getting a divorce and his ex was moving out to live with her boyfriend, he went over his finances and decided he didn't have that much money. So we began going Dutch for everything.

My issue is that now when we go out together, everything is 50/50. If he pays for dinner (which is usually splitting appetizers and a couple of drinks) and then go out for a drink somewhere after, he will wait for me to pick up the bill for the drinks. If he sleeps over my place I will make breakfast in the morning. We never go out.

All my friends are telling me that he is cheap and that he should take me out for a nice dinner once in a while. They say that I should not be expected to pay half all the time.

Am I dating a cheap man or am I being unrealistic to think that the guy should pay most of the time?

– Is He Cheap?, Wakefield

You are being very, very unrealistic. Men don't have to pay for everything. There are no rules about who does what. You've chosen to be with a guy who has made it clear that he has no disposable income. If you want to be spoiled by a big spender, you're in the wrong relationship.

Instead of worrying about who's paying for appetizers, spend some time thinking about how this relationship will work in six months or a year. Is he saving to make his situation easier? Can you see yourself living with him and sharing expenses?

Money aside, is he a generous person? Do you trust him? Is he becoming a partner?

After a year, it's time to consider the big picture.

– Meredith