My freshman year in college… moved into the dorm with two of my buddies from HS. Anyway one of them was pretty homophobic… he went on a trip to ASPEN where he met this girl and guy at a bar. They ended up hanging out a few nights in a row, long story short, the last night it became VERY clear that the guy wasnt dating the girl and was VERY interested in my roommate. Anyway he comes back from the trip and was freaked out by it because this guy had also said he had cousins living in LA (we were at school in Santa Barbara) and would be out to see them soon, maybe he’d stop by, etc. So being homophic as he was my buddy is all freaked that this guy is going to stalk him and come try to see him and sh*t. So of course I saw this as a great opportunity to f’ with him.
Since I knew all the details of what happened on the trip I hadc a great advantage - to impersonate the gay guy, Dale was his name. So I went about setting up false email accounts and an AIM account, all with “dale” used in the screen names/login. I immediately start messing with my roommate. Sending him emails, and talking to him whenever he got online w/AIM (most of those times we were siting in the same room, he had NO CLUE). I slowly built up with the stalking stuff over two weeks (even my other roommate didnt know!). Drew (my homophobic roomate) was really starting to freak out, cuz I started talking about how I (impersonating Dale) was going to come out to Cali and I wanted to see him. Then I kept adding info I had found out about where his dorm was, what room he was in what his phone number was etc. Being the only “computer guy” of the group he kept coming to me: “dude, is it really possible for him to just find this info out about me?!” of course Im like yeah… really easy, just gotta know where to look, anyone could do it… 
Anyway I get it to the point where Im saying Im (Dale) going to come by the room one day (Cuz dale is now visiting in LA ;)). Drew is FREAKING OUT, he wants to call the police and talk to campus security, etc.
Im at class that afternoon, leaving him to freak out in the dorm room (he actually stayed in another room down the hall in case Dale showed up!). Well he stoped by our room to pick something up and it turned out in my rush to go to class I had left the AIM login screen open with “funkydale” as a user. I come back to:
“HOLY SHT!!! YOURE FUNKY DALE, YOURE FUNKY DALE, you PRCK…etc, etc”
I was crying for like the rest of the day I was laughing so hard, 4 years later we still give him crap about it!
I can definitly say, I will never top that. It was so well planned, and perfectly played out… in short: I AM AWESOME!!!
peace