Man, this is a great post. Really made me think. I'm not sure what I actually have to say about it without just talking about myself a bunch, which I'm probably going to do anyway -- but it really resonates with me because I was I guess the class clown, or that's not right, it was more like I had just the right attitude throughout school to get laughs whenever I talked. I'm pretty good with stories, my friends always told me to go into standup but I never liked the medium because nothing comes up organically.

Today I made a room of 30 people who barely know me laugh hard during a meeting with a bit of improv'd back and forth. I think it's all timing and delivery, really, not content. If you look at the things every day that make you laugh out loud, how many of them are funny because they're clever? Clever things make people grin or nod, not laugh. It's all situational and contextual humor. For every funny thing I say in a group setting, I swallow a dozen, which is hard, and takes practice, and is the number one thing people don't understand I think. You can always tell when someone's trying too hard to get a joke in, right? And it sucks? Yeah.

A lot of it is knowing your audience. If you're midway through a story and you can tell it's shit -- we've all been there -- a) you misjudged your audience to begin with, probably, and b) for god's sake don't finish the story, find some way to defy expectations. You've also got to know when to laugh along with what you're saying and when to deliver it straight-faced. Both can save jokes that seem headed to hell.

It never really occurred to me how much of a science humor is. I've never deconstructed it before, I usually just act this way. People always talk about how much they hated 6th through 12th grades because they were way too self-aware. Humor is the best -- only? -- way to combat that feeling. Laughing at yourself is part of it, being able to laugh at the world is vastly more important.

I think that's enough of me rambling about humor for tonight.

EDIT: I just read what Kaius wrote and it made a ton of sense to me. Very similar. I wonder if I consciously forced myself to be funny at an early age and just can't remember. My parents both have what I consider to be excellent comedic timing so if I did it was probably to be more like them.

EDIT2: I also agree bigtime with onehunna and @rezzej@ -- observation and a wide range of experience can only help. A witty 13-year-old is a rare thing; they simply haven't ingested enough comedy themselves to understand how human humor works.