I guess I should jump back in here. As I mentioned before I know my short has some problems, but it got the job done. That it doesn't measure up to the standards of "True Geniuses" like Gary doesn't really bother me. By the way, that True Geniuses comment pretty much confirms that you are the same guy who was on the Nicholl's Fellowship Facebook page wreaking havoc.
I think it's great that you think I'm still a kid. After 20 years in the business I must look pretty good for my age.
And as for Laurel and Hardy and Chaplin and Buster Keaton, I studied them all in Film school, but that wasn't what I was going for here. In fact I was trying to avoid the whole pratfall and silly face approach to this. That's not funny to me. I had a guy on my crew who kept telling me to get the actor to go bigger with stuff, but I just wanted him to pull it back in. I'm more into subtlety in humor, like you might see in a Coen Brothers film.
Everyone has their own tastes. Mine are the opposite of Gary's.
I would have added two more layers to your short.
I'd have had an opening scene with the prospect of going in three directions then I'd have somehow made all three plotlines converge at the end.
For example ...
1. How to get the dry-wall in the dumpster.
2. How to tell the wife you have a mistress.
3. How to tell the neighbor his wife is the mistress.
A opening Voice Over seems the only way to start this way.
"Although I was looking out the window at my neighbors dumpster calculating the amount of time it would take me to rush over and dump the drywall in it, I had a few other things on my mind: 1. How to tell the wife I was dating her best friend, and (2) How to tell the neighbor it was his wife I was dating."
It really doesn't matter what the three plotlines are, but it should be three.
Now the challenge becomes not merely rendering a straight-forward plot the way you did, but forcing yourself to somehow include the two other ones.
The interesting thing about this method is even if you don't have a smidgen of humor, it forces you to be funny because how else can you bring these three things together?
Meanwhile, the audience is thinking "This is ridiculous. No way he can get resolution here."
So it also increases the interest factor three-fold.
You've given yourself a math problem to solve.
Don't worry about dialogue and scenes; don't even worry about humor or jokes. You just want to fit the three plotlines together -- if you can do that the humor will fall into place.
In fact, you'll find sometimes the more far-fetched the plotlines are, the more funny the short turns out.
For example:
1. How to get the drywall in the dumpster.
2. How to tell the wife you're gay.
3. You suddenly are able to speak Mandarin Chinese perfectly and don't know how that can be.
No way you can resolve those three things in a short without cooking-up a hilariously funny story.
Overblown and ridiculous dialog is good.