Had a 14yr old girl that lived next door for a while. I was 20-21 at the time. I used to babysit her when her family would go out of town for business (they worked for IBM) and things were cool. Kind of a brother/sister thing. Well, time goes by and she starts wanting to start going out. I'm not comfortable with it but she is and, frigheningly enough, so are her parents. I even got the "if you have sex be careful" talk from her dad. WTF? Okay whatever, I'll play along and see what happens. Anyway, one night she really tries for it and I can't do it. Seriously just don't sit right in my head. Well, I try talking to her about it and it doesn't work. I try to explaining things and it doesn't work. In the end, I turned up having to yell at her and pretty much break her heart to get it to sink in. It hurt me to do it and it sucked because I felt like I dragged her along for nothing, but I guess it was the right thing to do.

Yeah, that's probably the worst situation like that I've ever had.