That could definitely work. Moira's a lot more pragmatic about relationships after the divorce. She is wary of going down that road with someone who isn't committed to anything in life. Not that she's necessarily looking to get married again, but if she does, that's something that will have to be there. She wouldn't care that he's working in an entry level job, or didn't have any professional drive, but if he's aimless in life in general and he still needs time to figure that out then she wouldn't see them working out until he does.
How long do you want to say they were together and when? Were they thinking about moving in together or did they already?