His entourage of chicks, so confused...

I’m in my mid-twenties and have been friends with Tim for 5 years now. I met him in college. When we first met it was obvious that he approached me because he was attracted to me. I was young and naive and nothing ever happened back then… But to make that portion short, I ended up falling for him years ago anyway! Since then, we’ve become best friends. And I’m still in love with him. We have hooked up on various occastions, but we never broach that subject because I think we both have a silent mutual agreement not to jeopardize the friendship. A few months ago I started to suspect that he was developing feelings for me again. However, I moved in with him a few weeks ago because he BEGGED me to move in with him! Now Nothing sexual has happened between us since though. There are times when I’m convinced that he has feelings for me, and I KNOW I’m probably the most important female in his life… BUT my problem is he messes around with other girls. And he’s always been a flirt, which is part of the reason I never voiced my feelings for him. With all that’s happened between us, I’m just wondering if he’s just as confused as I am and thinks that I just view him as a friend!? I NEVER show my romantic feelings towards him at all. And pretend like I don’t give a damn when other girls are over. So is it possible that’s why he fools around with a bunch of seemingly meaningless girls? Or maybe the regulars aren’t meaningless? And It recently seems like he tries to gage my reactions when other chicks are around, to see if I’m getting pissed or jealous. Because neither one of us are the type to be open with our emotions. So my question is… How can I tell if he does (even possibly) have feelings for me? Is he just confused by me, as I am him? And with the whole living together situation now, if I finally do decide to tell him after all these years how I feel, how could I do that??! Thanks so much in advance! Any response is much appreciated!