Making sense out of it is a mistake!!

So this is one of the conversations that I really liked in a TV show and it goes like this:
"Ok yes it's a mistake.I know it's a mistake. But there are certain things in life where you know it's a mistake, but u don't really know it's a mistake because the only way to really know it's the mistake is to make the mistake and look back and say "Yep. That was a mistake".So really, the bigger mistake would be to not make the mistake because then you go your whole life not really knowing if something is a mistake or not. Does any of this makes sense to you?"

Would any one of you like to guess the TV show and the characters involved in this conversation? ;)