We have slept together, and I’m not crazy I’m special no wait maybe I’m crazy I have to talk to myself about this hold on shirt every time it’s intense and emotional, and he freaks out. Both of our relationships always fail. I want to be with him or move on. Should I tell him I’m in love with him? If you don’t say anything you’re pretty much guaranteed a spot on the sidelines watching him date other women and never knowing what might have happened. Chances are after this much time if he really wanted to be with you then he would be but at the same time maybe you scare him. You’ve been friends for 5 years now, it’s not like he just used you for a time in his life that was convenient and moved on.