My Debt-Free Boyfriend Nags Me 24/7 About My Student Loans From Law School

An unhappy looking woman turns away from a man who is talking angrily.
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Dear Penny,

I just graduated from law school. I have a lot of student loan debt, but I don’t have any debt from undergrad. My boyfriend is debt-free. I just took the bar exam, and I’m looking forward to starting work soon. For me, this is a huge accomplishment.

My boyfriend is constantly worried about my student loan debt and doesn’t understand what I’ve achieved. After three years together, he’s coming around to the idea that, although law school wasn’t something he would have ever chosen for himself, it was the right choice for me. He makes it clear, however, that he still thinks it was a bad choice.

How can I get him to stop worrying about my debt 24/7? We aren’t married, and this makes me reluctant to be in any relationship with him — let alone a long-term one. I’m confident that over time, and with the right goal setting and financial advice, I will pay these loans off. And the extra stress from him is so unwelcome.


Dear E.,

If this guy can’t support your career path, can you trust him with any other part of your life? I’m trying to imagine daily life with your boyfriend. If you came home from the hair salon with bangs, would he tell you he didn’t like them every morning until you grew them out? If you go out to dinner and order a cheeseburger, is he going to comment about your cholesterol every time you take a bite?

You may think I’m being hyperbolic, but look at the situation: It sounds like you’ve been together since around the time you started law school. The entire time you worked on your law degree, this man was breathing down your neck.

I can only imagine how many ways you’ve tried to reason with him. I can only imagine the stress his judgment added to an already strenuous course of study. You even said in your letter that while he has finally “come around” to the idea that law school was right for you, he still maintains it was a bad choice.

You know what else is a bad choice? Your boyfriend. If all he can do is criticize your chosen career field and the education required to pursue it, he doesn’t deserve your time and energy.

If this were a new relationship and he was wary of getting tied up in your debt, I’d understand his reluctance. But he’s been on your back about this for years, and I’m not sure how you haven’t grown tired of it far sooner.

I’m much more interested in watching your career develop than I am in watching this relationship struggle along.

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Lisa Rowan is a personal finance expert and senior writer at The Penny Hoarder, and the voice behind Dear Penny. For more practical money tips, visit