Oh, now I remember the stupidest thing I ever did, it didn't register because the consequences were almost nil.
I was a sophomore in college and our campus is on a hill. I live in the oldest dorms in school at the bottom of the hill, called the pit. It is all single rooms that used to be doubles. I decided I want a lounge chair to sit in and listen to music in in the dark. I noticed some up on the middle of campus in a lounge that I thought were good. My reasoning was, since drunk people get away with stealing stuff all the time at our school, that a sober me could easily get the chair.
So one saturday night, around 2AM, I mention my plan to a friend when I was in his dorm on the hill, that I want to go steal a chair from the louge nearby. He agrees to help me with it.
So, I go to the lounge, grab a chair and my friend goes outside to keep an eye out. Now the doors are narrow and even though they're double doors they have a vertical divider. So I'm trying to squeeze this chair though by myself (hey I'm big, i can do it) and my friend does a lousy job on lookout, and an RA just walking by stops and sees me holding the lounge chair in the doorway. He just stops, looks at me, and points, indicating for me to return the chair. I do so, and regroup with my friend, thinking this sucks.
Well, we try again 20 minutes later and get it out the building, now I have to get it to the path that leads down the hill (the pit path) through the woods, and to the pit. Well said path is about 100 yards away so I start to dash to it, carrying the chair. Right by the path is another dorm, I have to round that side of the building by the trash cans to get to the path. Right then, a van comes flying up the pit path, with a yellow rolling light on top of it. I never saw a car drive on the path but it could fit. My spidey sense kicks in, and I drop the chair by the trash cans, and hide behind the building.
The dorm is H-shaped, and I droppped the chair at one of the corners of the H, me and my friend duck around the other side of the dorm hiding near the woods, and like we're in some x-files episode we see flashlights waving around the nearby trees in our direction. So we make our way all around the dorm, get back to the chair and some drunk kids are going into the dorm pointing to each other and going "hey, don't you want a chair?" and such, but ignore it. I pick up the chair, noticed I broke one of the feet off of it when I dropped it, and continute down the pit path. I had no idea what was up with the van and flashlights, but they were gone now.
So while I lumber down the path with the chair, I discuss with my friend what we would tell someone if were we caught with the chair. We pass a few drunks on the path and they don't care about it. Once i reach the bottom of the path, all I have to do is cross a small road, go down some steps and get in the stairwell of my dorm, and up one flight of stairs is my dorm, right by the stairwell. We get in the stairwell, and I caught a glimpse of car headlights on the road and think nothing of it. I stop at the landing and hand the chair to my friend so I can get my keys out, and as I go up the stairs, I hear the door to the stairwell open and a deep voice say, "drop the chair."
I come back down and my friend sets the chair down, two campus saftey guys are there. so they're like "what are you doing?" My friend is tacit, so I employ my great verbal skills from roleplaying games, and tell him, "well, we saw this chair up by the trash cans up by the dorms, it looked like it was broken (I point to the foot i broke), so we figured it was a thow-out and decided to take it. The guy may think I'm lying but it doesn't matter, he takes our names and student numbers, but nothing ever comes of it. They say the saw the chair there too so they don't know if we're lying. The stupid campus safety guy is then bewildered trying to determine where the chair goes, even though "grahm hall lounge" is engraved inside the legs. He deduces out loud: "this is definitely one of our chairs, a LOUNGE chair." They think it goes to the dorm I dropped it at, when it goes to a different lounge. Great, I was caught by freaking morons.
The epic struggle to get the chair failed, I guess drunk people in school are lucky or something. That was probably the stupidest thing I ever did, since when I was home I found a better chair that fit the bill used for 20 bucks. Yeah and 2AM on a saturday at college isn't late enough, I should have picked 5AM. And the lounge I was stealing the chair from and the door i had to suqeeze trhough was right next to the door of the RDs room, they probably called campus safety.