Sorry but I had to do it with these stories.
Mine aren't as entertaining; I haven't done many stupid things which sort of sucks because now I have no stories to tell.
Stupid teenage thing #1: I was 15/16 and it was after midnight and 2 of my guy friends wanted me to come hang out with them. Of course I had a curfew, so I told them I would go inside, fake going to bed and come out in 15 minutes. My parents were in bed, so I waited for a bit, and then went into the laundry to sneak out through the window (which I had done before successfully). The window was rectangular and not very high. I had to climb on top of the freezer to get out. So while crawling through, the interior window came off the hooks and CRASHED down on the freezer and then on the floor. I wasn't stuck, but I was freaking out. Nothing I could do now. My mom came downstairs, asked what I was doing. What could I say? "I was trying to sneak out." Got a HUGE yelling from that from my dad because I was a straight A student, squeaky clean record.
Bigger stupid teenage thing #2: I went to the wrong college. Applied to a media program, would have definite job afterwards at a news station, but I got turned down because the course was too full. Decided I should be going to college that Fall, and applied to an art program at another school. Biggest waste of time and money ever. I dropped out after one year and now I'm broke, unemployed and sitting on TFP at 5:13am
But yeah, so far biggest mistake of my life that was.... Worst thing was, in the middle of the crappy art program I got a letter from the first school saying they could accept me for the winter semester. Oh THANKS, now I have no tuition money. Damn.