@Crazymanatuca21 - If you want someone to be a roommate they can't have any romantic interests or partners, no kids either I'm pretty sure. I don't know why (it's stupid, I assume it's working around some awkward code or something) but it's true, the other day I was trying to get two of my sims friends to be his roommates and it wasn't working, then I realised the two friends both had romantic interests. My sim has a high social networking skill so I used to relationship transmogrifier app to change them from romantic interests to friends and then I was instantly able to ask the two sims to be roommates. You could have the same problem.