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.
Funny Moments: In "Arm-prins", Greg has Sammy watch a VHS of Blue's Clues while he runs to the bathroom. Turns out he really wants to watch it, as Greg is forced to sit through it over 20 times. This eventually leads to him dreaming about being stuck in Steve's house.
At the end, Kim discovers Steve Burns is in her bed, and they make out.....in front of Greg.
Hilarious in Hindsight: Greg tells Jimmy to stop thinking about sex, to which Jimmy says "That's like Tiger Woods not thinking about sex." Now fast forward to 2010.
In one episode, Jimmy unintentionally tells Kevin Smith that his latest film (a WW2 comedy) sucks, at first Smith gets offended and demands an apology, but then he later admits to Jimmy that his film really does suck and he ends getting more funding to do a different film. A very similar scenario ended up happening with Smith in real life, after Smith directed Cop Out, Smith was pissed at critics for the negative reviews, then he later admitted the film really wasn't very good, and that was a big part of his decision to make Red State.
Played straight at first, when Greg gets tickets for the NCAA Championship game but Kim guilts him into attending her grandmother's birthday party instead.
Next, it was deconstructed by Christine when Greg gave Jimmy the tickets. She got mad at Jimmy for trying to get out of the party, but she then explained that she really didn't care what he did...she just planned to hold it over his head.
Then, it was initially subverted when Greg missed an important photo...the entire reason he couldn't go to the game...because Kim made him go buy ice. Although initially furious, Greg starts to enjoy the guilt being on the other foot.
Finally, Jimmy and Billy come back from the game and told him how miserable it was and what a terrible time he would have had (which was a boldfaced lie intended to lessen Jimmy's punishment from Christine). This double-subverted it, with Kim once again assuming the right.
Squick: During the episode Speed Dating, Billy asks Jimmy to go on speed dating with him for moral support, a proposition that Christine refuses to approve of — that is, until Jimmy tells her that Billy spends many dateless nights fantasizing himself with her, a revelation that prompts Christine to change her mind at once.
The Woobie: Greg, certainly during his childhood years.