Your OCD may be contributing, but other wise, this is 100% normal. Your in collage, your discovering yourself. I went through the same thing. You don't know who you are, so you shift through all the things you could be. Looking at things, not as they occur, but through the "Middleverse" looking at them from above, and over analyzing everything. How things could have turned out if you'd done this, or that, instead of just going along the liner path of things. I was the same, if I said something that thought I shouldn't have, I'd focus on it for day's. Turning over and over in my head till something else went wrong. Now I realize that the things I worried about, where insignificant. I made people laugh, cause that's easy. People are sure to like you when your funny, I played the jokester for years, but that wasn't me either. I made friends but making them and keeping them where to different things, they liked me for something I wasn't. So I wore a facade every time I was with them. I only had one really true friend besides my sisters. I didn't know who I was, so I explored, and felt myself out, and little by little, I got to know the stranger that was me. So my advice at the end of this ramble is simply this. Try to be more honest with the people around you. Don't just play the one dimensional jokester, let them get to know you, as you get to know you, explore. Try not to think of what could be, and think about what is. But the person above has a good point, I'm just drawing from my experience, I'm probably the last person who should be giving advice. You should try to seek professional help if things don't get better.
Good luck