Our advice columnists have heard it all over the years—so we’re diving into the Pay Dirt archives to share classic letters with our readers. Submit your own questions about money here . (It’s anonymous!)

Dear Pay Dirt,

I am a medical student in my 30s. I live with my boyfriend, “John,” who is a registered nurse. Neither of us have student loans or debt other than our credit card. My father still helps me with expenses—not a lot, but I have always had an “allowance.” John pays for all the house expenses, as I don’t really “work.” I do part-time side jobs, but I do pay for most of the groceries and take care of the house. We talk about marriage all the time, and once I work in a hospital, I know I will be making the same or more than him. But there’s a problem.

He spends a lot. By

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