Paul Graham recently mentioned that one of the characteristics Y Combinator looks for is "naughtiness" -- an intolerance for bureaucratic rules, a history of beating the system. Go read about it here: (http://paulgraham.com/founders.html)
So what are your stories?
Some years ago, my friend and I decided to kick off the night by drinking some beer in a park, downtown Montreal. After a few minutes, it started raining like hell. We had to get inside somewhere and the closest place was a university building which was "fortunately" still opened. We went inside and walked by the security, each carefully dissimulating our beer through our jacket. After wandering some time through the hallways, we finally found an unlocked classroom to finish our booze. Once done, we slowly walked back to the main entrance. We would soon realize that time had flied by and the building was long closed.
Fortunately there was still a security guy. We kindly asked him if he could unlock the door for us. Of course, we looked somewhat drunk and he asked us, on an authoritative tone, what we were doing here. My friend came up with the lamest lie. The guy wasn't stupid and obviously knew we were hiding something. By that time, another security guy had came by. "I have to get us out of the shit", I thought to myself. I took all my courage and asked: "Ok, so you won't let us out just because we are gay?". The guy became visibly panicked, probably frightened to lose his job over homophobia. He almost apologized and quickly let us out. I was really proud of social engineering our way out of this delicate situation. My friend wasn't, he started yelling incoherently at me. I told him to get over it: "Who cares if he thinks you're gay? You're never going to see him again". I was wrong. Remember the second security guy who was standing there all along? It happened to be a friend of his very catholic father.