I think her name was Candy. (j/k)
Seriously, I'm not sure what the dumbest thing I've ever done was, but I'm fairly sure it had to have been in my freshman year of college, in which I did such things as:
Stole the light bar from a police car
Took 36 shopping carts from a local supermarket parking lot and arranged them in a 'cart corral' type of structure outside a fellow student's window
Made homemade thermite and used it to weld shut the door to the room of a fellow student I really did not like
Dismantled a non-functioning overhead traffic signal, brought it back to the dorm, set it up at a crossing of hallways, and rewired it on a timing circuit so it did the green-red-yellow signal pattern with the correct timing. Other students actually followed the "rules" of the pattern - only walking down the hall when the light was green on their "side."
Went out in -13 degree Farenheit weather at 9:30 p.m. with four other guys on a quest to find "The Holy Searchlight," spending 3 hours traipsing all over the city trying to figure out where the searchlights we saw off in the distance were. Finally found them advertising the opening of a gas station. On the way back, noted someone had hit a stop sign and knocked the thing over. The five of us did not have any equipment with us to remove the sign from the signpole, so we picked the whole thing up and brought it back to the dorm.
Took a 2-pound block of sodium from the chemistry lab, brought it to the nearby pond, and threw it in. WHOOM!
I should probably add I did all this completely straight and sober.