OP did ask for the dumbest thing I've done....
My cousin and I (teenagers, of course) were about 30 feet apart and kind of herding the bear though the Alaska woods. Eventually, we lost the bear - so I walked over to my cousin - as I passed one of the trees, the bear took off running from behind it. We let it go since it let us go.
We also tried to chase whales in a 12ft skiff with a 6 horse outboard.
Come to think of it, we also tried to hunt in a huge flock of geese that was sitting on a beach - we ended up on opposite sides of the flock firing 22 pistols at the birds. Missed all the birds and each other.
I'm not sure how I survived being a teenager.