“He does not seem to be trying very hard to get a job.”

Maybe that’s true, but it’s also possible he’s looking for work all day long. A friend on the job hunt once told me she’d stopped updating people about every application and resume sent because she’d wind up having to answer the most frustrating questions: “Did it happen?” “Did you hear back?” “Any word?” It was deflating and exhausting, so she decided to let people know about jobs when she was closer to getting them. I understood and started to ask a better question: “Anything I can do to help?”

I don’t know what your boyfriend is up to, but … can we assume the best of him? That he is trying to figure this out for himself?

I do think it’s time for a broad conversation about money because finding a job can take a long time. Even if he gets some interviews and an offer, a start date might not be immediate. You need to talk about the plan for March, April, and May. You should also think about how you’re approaching this conversation. Are you a partner or a roommate?

I don’t know what an ultimatum would look like, but I don’t recommend trying one right now. It’s better to have an honest talk about how you can support each other.

– Meredith

Readers? How do you approach conversations about money and employment?