Reddit top voted answers...
I worked as a tower hand for a construction company. I used to take of my lanyard and move between booms(500-600feet up.) I also would slide down the outside legs untethered because it was faster than climbing down the ladder. I cringe when I think about that there was zero chance of survival if I fell.
Timeshare presentation. I now know what hell is like. 8 hours of my life I'll never get back.
And of course the "free trip" was impossible to get. "We will call you on Monday sometime in the next two months, then you need to fly out on Tuesday and come back Wednesday."
Back in the days before soft contact lenses you were supposed to clean them with hydrogen peroxide and then use a special neutralizer tablet afterwards.
I forgot to use the neutralizer before I put my contacts in. Hydrogen peroxide in your eye HURTS!
Asking a woman when her baby is due.
Doesn't really need a story. It went as imagined.
Loaning money to a friend.
Lost the money and the friend. Not a very good deal
Rode an Amtrak train from New Orleans to Washington DC. I thought I was a prodigy by choosing coach seating over a sleeper car or flying as I was saving some money by doing so.
Jump forward to 25 hours in the same seat, dude next to me pulling a Germany VS Poland invasion of the armrest, baby screaming all night in the back of the car and I couldn't sleep. The Toilet situation had deteriorated onboarrd to the point where I would use elbows and my boots to open and close the door and flush the toilet as my fellow riders were baffled by the concept of flushing and utilizing a trash bin for paper towels.
I've been awake 25 hours by this point and it's 3:45am.
If I ever do this, it's gonna be in a sleeper car, fuck the savings.
Murder on the Orient Express had the right idea.