These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Anti-Climax: After months of waiting for a new episode after 69's cliffhanger, and then fans having to get the DVD to see it, who's the Hummel Figurine? Melvin. That's it. And Ask That Guy just takes questions like normal straight after.
Ass Pull: His death of being asked if he wants to ask a question and then blowing up, with Chester being the one to tell the audience he's not coming back. Plenty of people have blown up in the CA universe, but for some reason this one sticks.
Big Lipped Alligator Moment: In episode 63, That Guy is hit with a giant wooden hammer from off-screen. When he attempts to answer the next question, he's hit with it again.
The entire YardOz segment, which is a parody of Zardoz featuring a giant floating head in the sky that tries to convince That Guy to engage in self mutilation for no apparent reason, is ignored, and then the episode goes on without a single reference to what the hell just happened. At least it explains how he got a new pipe.
"I'm going to be a monkey now".
Cargo Envy: People have gone on record saying they'd love to be that pipe.
Crosses the Line Twice: Pretty much 'every single word that comes out of his mouth. It's impossible to find a single episode that does not include something that would make the show ban worthy in some countries.
And yet somehow, he managed to be even more horrifyingly indecent by inviting Sage to answer questions.
Example: For his ninth video, he casually greeted his viewers:
Fanon: The gloriously nutty fanfic fandom has decided that the porn movie "Bunny Does Dallas" involved a man in a bunny suit raping a Bound and Gagged Critic with a carrot.
Fridge Horror: He interacts far more with his creator (non-verbally anyway) than Critic ever did. If he ever gets through the fourth wall, then Doug is really not to going to have a good time.
His voice getting more effected. He's rapidly losing the cool he once had, to tries to compensate by using a tone that went well beyond reasonable poshness ages ago.
Fridge Logic: How on earth did he manage to get into heaven? Twice?
Justified by God Is Evil, since apparently Ask That Guy has been considered appropriate to be an evangelist.
"Funny Aneurysm" Moment: In episode 31, he made a joke about all the scary freaks of nature who now know who he is. Let's just say Doug's fanbase has got much creepier since then.
If Doug's marriage ever ends, regardless of if by divorce or death, then episode 54 will appear this way. Hopefully, though, this won't happen for a very very long time.
Growing the Beard: Episode 4 was when his sadism and issues really started to appear. Before that, he was just a suave-but-wacky moron who answered every question wrong.
A lot of people think the beard grew again in episode 53 when he moved locations, as there was more focus on Villainous Breakdowns, interactions with other people and giving him extra Hidden Depths.
Harsher in Hindsight: In an early episode he has a breakdown about dying alone and forgotten because he's so intelligent, but then snaps back to claim he was just joking. Fast forward to now and he's having constant breakdowns because his humanity won't stop coming out.
Hilarious in Hindsight: In episode 27, he says people only watch his show for soft porn. About twenty episodes later, well, just have a look at the fanservice entry.
I Knew It: His parents were badly abusive. Cue the gasps of surprise from absolutely nobody.
Jerkass Woobie: Occasionally, when he realizes how sick and twisted he is and gets upset.
His Sanity Slippage recently seems to drive home the idea that there really is a pathetic little boy underneath all that monstrousness.
LGBT Fanbase: Far more sexual and fetishizing than the casual Everyone Is Bi style of Demo Reel, but still one of the most popular shows for it thanks to Doug's willingness to fellate anything phallic he can find.
Most Annoying Sound: "THIS IS THE MOST ANNOYING SONG IN THE WORLD!" It sounds funny the first few times it plays, but when he makes that song the background music for the whole episode, you will want to stab your eardrums with an icepick by the time the credits roll. Which is kind of the point.
Nightmare Fuel: In episode 63, when asked if he ever attempted a world record, he says "I'm the only person in the world that can do this" and then he turns into a floating brain with ominous demonic sounds play while he screams in terror.
They Wasted a Perfectly Good Character: In the second half of Ask That Guy's run, he had a cutely sadomasochistic canon-sleeping-together relationship with a narrator who became a character (of the Love Martyr kind) of his own. But in the finale, there's no reference to the relationship and ATG is oddly sexless.
The Woobie: Pity the poor narrator. Although he's not completely without fault, he never says anything against the Ax-Crazy questions often given, or tries to stop Ask That Guy's killing sprees.
The GPS got proposed to, married, had her husband leave in a temper tantrum and then come back to shoot her all in one day.