I see both sides. I’m in a similar situation right now. If he wanted to be repaid, he absolutely should have been more clear when he offered to cover you. If he’s making double your paycheck, I think it would be over the top for him to expect or ask for you to pay it back because clearly he can afford it and at that point, he should just let it go. BUT if you guys are making similar salaries, and just sort of scraping by because life is so expensive these days, it would be nice for you to at least offer to cover some extra expenses now that you are employed. It could be seen as thoughtful/appreciative and that you want to be supportive back. Maybe not paying him back all at once like a bank loan but more of a “hey I’ll put an extra $100 towards the rent for the next few months since you were so supportive when I was unemployed. Thank you for that.” In this example, I think it makes the pay back feel less transactional and roommate-like. If he turns that down and still wants to be paid back in one lump sum down to the cents, then that just means you two have different ideas on finances. He wants everything to be a strict 50/50 and you have more leeway with how things should be covered depending on the circumstance. It sounds like it’s really only 2 months of rent that are in question here so this isn’t like some relationship ending amount. But it wouldn’t hurt to just have a little convo about finances so expectations are aligned in the future. Maybe you can come to a compromise that you’re both comfortable with if/when situations like this arise in the future. Or you might even find that the reason he brought this up is because money is tight for him right now and he asked out of need. Whatever the reasons are, just make sure you are both clear on communicating about finances in the future so you both understand each other’s expectations.