Funny: Ib

  • When Ib slaps Garry back to sanity if he fails the doll room.
    • The funny part? You can slap him TWICE
  • The first time you meet Garry. He tells Ib that he's going to lead the way because he can't let a girl get into trouble and that he's the more capable one... and then he freaks out when a painting spits at him.
  • When Ib doesn't know a word she's reading it appears as "???". When Garry is with her, you can see the words she normally doesn't know... with one exception.
    "??? by the ???, I ??? my finger over her beautiful ??? ... With her ??? she..."
    Garry: (closes the book) "... Don't read this kind of stuff until you get older."
    • If you go back with Mary in your party:
    Mary: "I wonder what this says? Read it for me, Garry..."
    Garry: "... I'd rather not."
    Mary: "Huuuh, why? I wanna know!"
    Garry: "... It's too soon for you two."
  • If you do manage to find the key and not fail the doll room Garry unlocks the door and runs to the far end of the room outside. Even going near the door afterwards will make him remark,
    Garry: "I don't want to go near that room."
  • Some of responses to the artworks can be amusing, like trying to ask Garry what "Abstract Art" is supposed to be or if Mary is present when looking at "Fleeting Thoughts on a Moonlit Night".
    Mary: "Wooow, pretty! I wonder what this is?
    Garry: "A cherry blossom? Plum tree? I'm not too sure which...
    Mary: "Hmm... Can you eat it?"
    Garry: "... Er. It's a tree, dear."
    Mary: "Ooopsie!"
  • Early in the game, there is a painted woman who is nude, and if you open the curtain hiding her she gets angry and slaps you. In Version 1.04, however, going back there with Garry causes her to slap him instead.
  • In Version 1.04, returning to the room with the ant while Garry is present leads to the two of them having a really funny argument.
  • Statues are a great inconvenience in the game. Garry has to constantly push them out of the way and Ib and Mary are simply too small to even attempt such a thing. But then on the "A Painting's Demise" ending path, you wind up playing as Mary, who... politely asks a statue to move out of the way. And it works.
  • While for the most part Mary's breakdown in the brown area is very upsetting, some of the things that Mary can say during this are quite fun. At one point she asks Ib if she's ever chomped down on a crayon, and declares that it tastes really bad.
  • In the Bonus Dungeon, Garry and Ib at one point find themselves almost entirely in the dark. Some sort of decoration falls over, causing Garry to scream, and you are given the option of telling him that his screaming is scarier than the thing falling over was.
  • Similarly to the scene where they find a book that Garry will not let Ib or Mary read because he thinks it's not appropriate for people their age, there's a part in the Bonus Dungeon where Ib and Garry come across a painting called "Tryst After Death". Ib asks Garry what a tryst is.
    Garry: "Well, it's something like a secret meeting with someone you like. Huh? Why is it secret? W-well, er, I wonder... it could be any number of reasons!"
  • You can have Ib stare at a lot of things. Stare at a painting. Stare at a congested eye in the floor (which stares back at you). Stare at Garry - multiple times. Garry thinks it's creepy, and he and Mary both find it a tad annoying. But then, late in the game, staring at something turns out to be helpful. (Staring at the lake in the Sketchbook, after you've opened Pandora's Box, reveals part of the code for the puzzle inside the frozen house.)
  • If you get to the part where you play as Mary the menu screen changes style to a white page with badly drawn crayon to list her equipment. It isn't quite as funny once it starts to get darker, though.
  • When in the library, you can talk to Garry, and occasionally, he'll ask you something, prompting a decision of questions you can ask him. Among these questions is "Why do you talk like a lady?" Garry will not get offended if you ask this, but the fact that it's even an option to begin with is pretty hilarious.
  • In the Bonus Dungeon, the little black stick figure riding on the bird can be seen this way. It's almost like watching someone on a leaping mechanical bull ride.
  • Also, the white ant in the dungeon will turn down candy if Ib offers it to him as a snack, saying that it's too salty for him. Ants must have weird taste buds.