My conundrum is that my lease runs out in less than 3 months, at the end of May, and I would really, really, REALLY love to move in with him at that time. How should I bring it up? I wasn't really planning on trying to broach the subject till April at the earliest, but I am just trying to figure out how to approach the issue. We are pretty good at communicating honestly and directly with each other, but I feel like this is a delicate issue, and I don't want to push him into something that he's not comfortable with. Should I just mention every now and then that my lease is out in May, complain freely about my roommate (so dropping hints)? Or should I just go in for the kill and ask if I can move in?
I have never been in a live-in relationship, so just don't know how to proceed from this point. I would appreciate any advice from you lovely ladies, and heck, I'd like male input too!
I talked a lot about how my lease was going to run out, I wasn't sure where I would live because I needed to find a cheaper place somehow, I didn't have anyone that I could live with, I was so stressed out and worried about what to do, blah blah blah.... he took the bait, started thinking, and then tentatively said 'well you could move in with me, but here are all the issues that might come up as a result' (like my family finding out and raising h* for one, what to do with his then-current roommate, etc.). 
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