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Saying what if this would happen and knowing it would happen I look at that and I cringe at it

oh boy, the amount of things that i could answer this with that i'm not remembering at the moment

I once accidently locked myself out of my school. Take make things more embarrassing, my ex had to let me back in.

I got a pet dog, apparently dogs and skeletons don't mix well...
(so I had to get a skeledoggo, so I don't have to worry about running my fragile bones away lol)

My sister and I were goofing around in our living room, and then we bonked in to each other, and one of her teeth fell out. Still kind of feel bad about it.

being dumb

A while ago my brother just jumped into bed and he accidentally broke one of his permanent teeth, so he had to a get a fake one molded on it

OOF

The wooden bed frame

When I was playing Xbox as a kid, I found it annoying that each disc can only run one game. So, I got the brilliant idea of putting in two discs at once so I could switch games without changing discs.

Luckily, my parents were there to stop me in time

Same as Gawen.
Most of it happened before or during the first half of first grade.

It wasn't me who made the dumb decision, but I was involved. Me and some friends were playing capture the flag, but with extra rules so you do a battle with plastic lightsabers instead of tagging. The other team decided that their flag would be a glass jar filled with rocks. I don't know who approved this. But then I got it, and was close to the line dividing the sides, and a tripped, and it shattered.