One of my favorite blogs to read is called Dubious Quality. The blog seems to have two very important themes; one involving his son, Eli, and the other is heavily dedicated to video games and their quality.
I really enjoy reading his stories about his son, because he is going through what I was going through just a few years ago (his son is soon to be 9, mine is soon to be 14). He spends a lot of time telling his son what is or isn't "funny" and trying to teach him how to "be funny". I have had this exact same discussion with my son a million times.
One thing to understand is that my son does not see anything but black and white, which I am pretty sure we have discussed here before. Not that he is color blind, but he is a very literal person. He is very good at math, because it deals in absolutes. He struggles with English because it is very subjective...it is just the way he is. He is a WHIZ at things with patterns. I have never seen anyone better at the game Simon before...he is a master at it. I hate that game in ways that cannot be described, but he makes it look like Candy Land....but I digress.
Chandler (my son) is always trying to be funny, and he struggles with it a lot because there are so many different factors that go into "being funny". Timing, delivery, confidence, etc. all play a huge part in "being funny". His biggest problem is that he tries to reduce it to a formula, and expects it to work. Something like timing+deliver/confidence=funny....and he can't understand why some things fall flat.
He has a very sharp mind, and he can be very funny sometimes. I remember once when we were at a National Junior Honor Society induction ceremony and they were calling out the inductees in alpabetical order. There were two kids with the last name of "Ngyuen" in a row, and he leaned over and said, "Sounds like a Ngyuen-Ngyuen situation". I cracked up...that was funny! But immediately after he says something funny, he wants me to break it down and explain to him why it was funny, and I can't!
It actually has become kind of funny in a meta kind of way, because it makes me laugh at how he wants to know how it was funny. Then he wants to know why that was funny, and it just keeps steamrolling from there. Smeesh.