You take a risk on something with full confidence that you will succeed and nail it! This usually applies to some type of competition or posturing.
"Did he just strike out our best player with a blindfold on?!"
"He just got lucky."
"No way, man. That was definitely' Wintentional' for sure."
When you don't expect to have a good time but then are pleasantly surprised with how much fun you actually had.
When you plan for something to be fun or hilarious, but then something unexpected happens that makes it even better.
An accident or mishap that comes with hilarious results.
"My greatest 'funintentional' moment has to be when I poked holes in my older brother's condoms. Instead of ending up with one baby, he now has triplets and I'm the world's greatest uncle!
"I didn't think I'd enjoy going to a musical, but that was the most 'funintentional' night I've had in a long time!"
"Jess is the most 'funintentional' person I know. Just yesterday, she broke her phone in an attempt to prove that hers was more durable than mine!