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- The way the game kicks off without Ib really doing anything to trigger what happens. She's simply wandering through the gallery, looking at things like she's supposed to, when suddenly the lights flicker and she's stuck in a terrifying and deadly situation.
- Exactly what did Red Eyes actually do to Garry? If you fail the doll room puzzle, you see Red Eyes reaching out of its painting for him... and then the perspective automatically switches back to Ib, who is in a different area, so the player doesn't see what happens next. When you venture downstairs and find Garry, he's a rambling, psychologically traumatized mess with no memory of what happened, or the events leading up to it.
- In one room early in the game, there's a painting called "The Lady in Red". It appears to be an ordinary painting... until you walk away from it, and it tears itself off the wall and starts chasing you.
- One of the first puzzles involves heading into a hallway with a bunch of people with colored shirts in frames. There are six, and they give hints about where to look in the next room. All but one is lying, and you have find out who's telling the truth. Once you do that and find what you're looking for, you hear something from the hallway. Once you get out, all of the picture frames have red splattered all around them, and they're all wielding bloodstained weapons... except the truth-teller, who's completely gone from its frame. In a show of irony, they all yell "Liar!" It's really unnerving.
- Mary, the psychotic painted girl who wants to become real.
- There's an optional sequence you can encounter by switching back to Ib immediately after The Reveal... or barring that, completing the doll room event successfully. It's a three-part sequence, regarding Mary going off the deep end. First she runs out of the room to stab a mannequin head, which bleeds. Second, her sprite will visibly begin to follow Ib from behind — something that NEVER occurs anywhere else in the game, even in cut-scenes. Third, she'll wander around endlessly, ignoring the player completely. Couple this with some unnerving Madness Mantras and vaguely threatening dialogues and you've got the player completely freaked out.
- The dolls. THE. FREAKING. DOLLS.
- The simple fact that until near the end of the game, Ib can't see the dolls at all. Her mind replaces them with completely harmless bunnies, so she can't even see why Garry would find them unsettling.
- The doll that stalks Garry down a hallway. Her tendency to teleport around when you're not looking is more than a little spooky. Also, if you kick her, her head keeps following you.
- The Giant Doll, also known as "Red Eyes". It first appears in the alleged bunny room (pictured above), and continues to appear ominously in several of Garry's solo sequences under certain circumstances, sometimes peeking over the top of walls and pillars and looking back and forth. Then in the second doll room, the Giant Doll starts crawling out of a painting. If it catches Garry before he can escape the room, he is later found by Ib and Mary, traumatized and muttering incoherently. In a normal playthrough, Ib's able to snap him out of it, but if you really screwed up before that point, Ib can't save Garry and you end up with one or the other of the worst endings in the game.
- Even succeeding in the second doll room gets creepy; while Garry manages to escape the room, the thought that the dolls are still there is more than unsettling. Also, the split second before Garry escapes the room, the dolls suddenly all turn their heads at once. They don't look at Garry, they look at the player!
- In the regular art gallery, a dialogue choice with another art gallery patron reveals that 9-year-old Ib thought the headless mannequin statues were scary before they started attacking her in the phantom gallery.
- Those roses. When you take damage, they wilt. Fair enough, except it works the other way around too; Garry mentioned that before he met Ib, whenever his rose took damage, he'd notice physical wounds opening up on his skin. Imagine if you'd left your flower behind, never realizing its significance. If a monster found it, you could just be walking down the hallway when huge cuts start opening up on your body, and since you don't have a vase, it might never heal...
- Starting in Version 1.04, if you let Garry kick the mannequin head and return to the room opposite the one where you had to move the table... it's changed. There's a hanging, severed mannequin head dripping blood into a vase, a poster on the wall mentions that someone damaged the artwork, and behind it, someone's scribbled "Hanged Garry".
- And then in optional dialogue later on, Garry asks Ib if there's something around his neck...
- The Sketchbook World is already quite disturbing. Even more disturbing that Mary is actively looking for Ib and Garry, and at one point very nearly finds them. Even more disturbing after you open Pandora's Box and every once in a while sharp pointy objects randomly fly out at you. And then Mary does find you...
- The Reveal that Mary is a painting is disturbing in and of itself, but one of the things that makes it so frightening is that Garry learns about this while he is separated from the girls, meaning if Mary were to attack Ib right now, there would be nothing Garry could do about it.
- The mirror. If Garry kicked the mannequin head, checking the mirror after the Separation room will lead to some pretty scary images. Garry's own head may be blotted out (which only Ib can see), both Ib's and Garry's eyes will be scratched out with the word "EYE" scrawled all over the mirror, "NOFIRE" may be repeated to cover the mirror, and the word "Play?" may appear, written in crayon. Creeeepy.
- In the Grey Room with all of the Painted Ladies, if Garry kicked the mannequin head, the Hanged Man portrait can have a (random) case of Red Eyes, Take Warning.
- When Ib and Garry are captured in the Sketchbook world. One moment they're staring into a toy box, the next moment they've been shoved into it and find themselves trapped in an area filled with statues... and dolls... and mannequins... and more dolls... and more mannequins. To make things ever better, Ib's rose is missing. Depending on what story path you're on, either one of the dolls steals Ib's rose and gives it to Mary, and Garry ends up having to trade his rose to save Ib's life, or Ib finds her rose and discovers that the impact from the fall knocked all the petals off except one. And there's no vases in the toy box so no chance for Ib to recover her rose. Either way, you're in bad shape in this section.
- Carrie Careless and the Galette des Rois. A charming little storybook, drawn in crayon, about a little girl celebrating her birthday. There is a coin in one of the cake slices and she accidentally swallows it. But that's okay, because it was a lucky coin, so now she'll have good luck. Then one of the girl's friends goes back to her mother, and she can't find the key to the study now. The friend, realizing that they'd baked the key into the cake by mistake and Carrie had swallowed it instead of the coin, decides the best way to get the key back is to kill her. The end. It's also scary in a meta way, as some people have had it crash their game.
- The Dungeon, a Bonus Dungeon accessible after beating the game once, contains such charming things as discovering Garry's lighter is out of oil right when you're in a pitch-black room, a giant sleeping snake that you have to get past, giant flowers that grab Ib's ankles and eat her if she tries to walk by them, a painting named "Mistake" escaping its frame and wandering around, a vase that has blood in it for no apparent reason...
- Mistake would be creepy enough even if it wasn't trying to kill you: it almost looks like conjoined twins fused at the torso, if one of them had gotten their head cut off. And the way it comes alive is just as bad; Ib reads a label near the painting, saying "My heart goes to art. My spirit goes to my creations" (a quote from Guertena), and suddenly Mistake springs out of the painting and tries to chase Ib down. (May also induce Fridge Horror if you think enough about it. Is Guertena's spirit itself in Mistake?)
- The painting "Malice's True Form". You encounter it in a dark room, it makes sounds and moves slightly when you look at it closely, when you move away from it you hear something fall to the ground and it makes the weird noise again, then you go back to find that there's nothing in the frame that had held it. And then later you are in the area with the giant snake and find that "Malice's True Form" is right there in the hallway. Eek. It doesn't attack you, and it can't even harm you in any way, but it's still creepy as hell.
- It turns out to be perfectly okay, he really did need a rest and he woke back up just fine, but the part where Garry takes a nap is quite disturbing, especially when he says it feels like his legs are becoming one with the floor, or the "....." if you try to talk to him after that.
- It gets better. In the real world, there is an exhibit named "Fusion". It is a sculpture of a person whose legs are missing, so that it looks like the person is becoming one with the floor. To top it off, the sculpture is entirely blue.
- Even scarier is the sequence you have to go through before going to the secret room. Garry falls asleep, you can't go outside alone, and you've done possibly everything in that room until there's nothing to do until Gary wakes up. Of course, when you check on him, he's not waking up at all, and all of a sudden the next thing you know, the room and everything in it begins shaking about. Check on Gary during this and your dialogue choices are "Garry!" and "Wake up!", and choosing either will just prove to be futile no matter how many times Ib tries to wake Garry up in her state of panic. And since she can go through the Bonus Dungeon alone, imagine her freaking out during this with no one around to give her a sense of security.
- "Final Stage". It's a strange, diamond-shaped bed that Ib can sleep on, and she dreams about her birthday. Awful cute, right? Sleep on it too long, though, and Ib sleeps forever. "Ib All Alone". Notably, while Ib gets a "nostalgic feeling" from it, if Garry's with her at the time, he won't let her near it because he gets "a bad feeling" about it, and he's right.
- Not sleeping on it for too long can be almost as bad. If you wake up in time, you'll find that some of the petals of Ib's rose have fallen off. It really gives the player a sense of wow, that was a close call, and it removes any possible ambiguity to Ib's fate if she doesn't wake up in time...
- The "Welcome to the World of Guertena" ending. Garry loses his mind in the doll room, Ib is unable to bring him back to his senses, Ib has a breakdown over this, and Mary has grown so fond of Ib that she can't bear to go to the human world because it would mean parting with her. So she instead keeps Garry and Ib in her world. Forever. Not to mention she has a freaky Slasher Smile in the final scene.
- The ending A Painting's Demise is very disturbing. With Garry driven insane by the Doll Room and Ib too distraught to leave, Mary abandons them and leaves the Fabricated World. Only, as she steps into the "Alternate Gallery", the writing on the walls threatens and warns her not to leave. When she does step out into the "Real Gallery", there's no-one around and the Gallery's door out is locked. As Mary gets frightened and tries to find another way out, it slowly gets darker, and dark paint drips from the ceiling like blood. The "Embodiment of Spirit" rose sculpture is faded into a withered and grey husk with a warning about Mary's "fabricated heart", the poster advertising Guertena's Art Exhibition at the entrance has turned into an image of a face-down (dead?) Mary◊, the windows overflowing with a creepy bloodlike red liquid, the creepy crooked writing saying things like "B Y E B Y E M A R Y◊", the painting of "Abyss of the Deep" bleeding out into the Gallery, "A Well-Meaning Hell" turns into Tones of the Dark Gallery◊, and then if you repeatedly examine Mary's inventory screen as things get darker...
- The fake Garry, who appears if you're on the path for "Forgotten Portrait". When you get to the portal back to the real world, this guy appears, telling Ib there's another exit and trying to tempt her away from the portal painting. If you go along with him, you get "END: Ib All Alone", and if you refuse him and jump through the portal anyway, he suddenly lunges forward as if trying to grab you. Worse yet is the ending, Garry is dead and his corpse is displayed in a new painting in the gallery. Ib and possibly everyone who ever knew Garry forgets him. Ib gains absolutely nothing from the journey except maybe horrible nightmares she can never explain and a man lost his life. Who's to say that this isn't the first or last time this happened or will happen?
- Any of the "Ib All Alone" endings, but particularly the one you can get in the Bonus Dungeon, if you sleep too long on the artwork "Final Stage".
- The "Together Forever" ending, while cutesy, has its fair share of Fridge Horror. Garry is dead and becomes a painting like in the "Forgotten Painting" ending and everyone who knew he supposedly forgets him. Mary becomes real and is remembered as being Mary's sister. Ib and Mary become loving sisters and go on together. Okay, that's kinda cute and not too terrible except for Garry, but Mary is insane. Who's to say that her insanity just went way. Worse yet, she's violently insane. Becoming real may not be enough to fix her broken mind. It's entirely possible that she would grow up to be a serial killer, and even if she doesn't, that doesn't change the fact that the kind-hearted Garry had to die to let this crazy person have access to the real world.