All of the men I date are unemployed

Friday | December 19, 2025

Love Letters Dating

All of the men I date are unemployed

What’s on your mind about your relationship life? Friendships, romantic relationships, family? Send an anonymous question through the form – or email [email protected].

I have never dated a man with a legitimate job. I’ve always wanted to, of course, but they are always working on something or in between jobs. Or studying for a new degree.

I broke up with my last ex years ago and I thought I was being really intentional about dating, and now my current boyfriend is in school full-time and lives on government subsidies.

I run a very successful business. I feel like I want to be with this man, but our extreme opposite incomes makes me uncomfortable. If we have a trip, it’s assumed I’m paying. He says he doesn’t want to get married till he’s financially stable but will that ever happen?

Am I enabling him? Should we break up so he can figure it out on his own?

– Working

A breakup might help you figure out what you want.

He’s living his life, getting an education – with assistance – and thinking about how he can be more stable in the future. But you’re unhappy. You’re the one who seems to need space to consider your feelings and what you want for your life in 2026.

I want to say, for the record: I see no problem with one person supporting another, in a relationship, especially if a significant other/spouse is in school or has a profession that brings in less money.

I feel the need to say that because sometimes letter writers have formed opinions about financial support – and who should pay for what – based on other people’s expectations. If you don’t mind paying a loved one’s vacation, go for it.

If you want a more equal relationship, that’s another thing. Maybe it’s time to start over.

Take a break, or, at the very least, spend some time thinking about your happiness. You’re allowed to want your future plans to happen now. It would just require looking for someone who’s already living his best life, in the present.

– Meredith

Readers? Thoughts on dating people who earn less – or need more financial support?

What’s on your mind about your relationship life? Friendships, romantic relationships, family? Send an anonymous question through the form – or email [email protected].

Dating Money 🖤

Featured Comment

There is being unemployed and there is not working right now because there is a plan. If the current guy you are dating seems to have a plan–in school and will become a doctor, for example, that is one thing. If he is in school to avoid working and isn’t sure what he wants, that’s another.

sunalsorises Share Thoughts