Me and two of my friends burnt down an 18th century barn and flames were 4 stories high. We were all in grade school and nobody was hurt.

One of my other friends went cow tipping with a beat up unregistered K-car. Then smashed it into a tree and deliberately flipped it upside down all while getting drunk. They were 16.

Q: What's the dumbest thing you've done in your youth?

A: Back when I was in grade school, I think it was either 5th or 6th Grade, I developed this weird kleptomania streak.  It only lasted like 3 months, and it was mostly because I chickened out 2/3 of the way through, got caught each and every single time, and then got the royal bejeebus beaten out of me by my father and stepmother.  It was usually little things ($1, a pack of baseball cards, a Garfield notepad, stupid crap like that), and, really, I sucked at this.  I could never quite get the hang of lying, and my best-slash-only alibi up to that point was "I found it on the sidewalk".  So I have no idea whatsoever why, that summer, I thought I could get away with a $400 heist. 

I won't be telling you exactly what I did, because no I'm not giving those details on the internet.  I will only confirm the following facts:
- I got the living poo poo beaten out of me for it, seriously I ached for about a day
- I also got the holy fetch grounded on me, a grounding that wasn't lifted until months later when I moved in with my mother
- I also, for the first and only time in my life, genuinely deserved it
- Because, for the first and only time in my life, I actually got away with theft
- Also, I got away with keeping/spending it for like a whole month before I got caught
- Mostly though, it's because the money was for SICK KIDS and THAT IS HORRIBLE
- It's also why the charitable organization in question got their money back

I'd be amazed if anyone here could top that story.

I once stole an apple from a market with my cousin and it took quite some peer pressure from him :|

Now you are stealing things on the internet every day....

When I went to Disney land I told the bag checker that my aunt had a bomb in her purse.
The bag checker said, "oh don't say that!" and my uncle yelled at me.

I never saw my uncle again after that trip

I was suspended in first grade for pretending to fight a classmate during recess.

rowdytuesday gives new meaning to "go big or go home" LOL

I decided to spend a day doing homework, and didnt check this site, or go on the IRC

I really like the premise of this topic, so I will post one story at a time because I don't remember any singular event that is the dumbest so maybe doing this will jog my memory.

When I was like 8 years old I used to go out and throw/kick a football when I was bored because I knew I was destined to be the next great NFL player.  For some reason there was a tire in a tree at a good distance away, so it was a good benchmark for how my skills were developing.  Unfortunately this resulted in almost an entire minute spent to retrieve the ball each time, so I thought it would be a better idea to try to get it over the roof of my house instead since it was pretty high.  I put my skills to use, kicked the ball off the end of my foot and directly into the front screen door which broke the main panel.  I played it cool, said it was an accident and didn't get in trouble for ANYTHING also it never got fixed

I really like the premise of this topic, so I will post one story at a time because I don't remember any singular event that is the dumbest so maybe doing this will jog my memory.

When I was like 8 years old I used to go out and throw/kick a football when I was bored because I knew I was destined to be the next great NFL player.  For some reason there was a tire in a tree at a good distance away, so it was a good benchmark for how my skills were developing.  Unfortunately this resulted in almost an entire minute spent to retrieve the ball each time, so I thought it would be a better idea to try to get it over the roof of my house instead since it was pretty high.  I put my skills to use, kicked the ball off the end of my foot and directly into the front screen door which broke the main panel.  I played it cool, said it was an accident and didn't get in trouble for ANYTHING also it never got fixed

Most anticlimactic story ever

I always think that my stories don't compare because I never got punished for anything (that is why I was hesitant to post ITT)

I decided to spend a day doing homework, and didnt check this site, or go on the IRC

Thats real dumb.