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1'''As a Moments subpage, all spoilers are unmarked [[Administrivia/SpoilersOff as per policy.]] Administrivia/YouHaveBeenWarned.'''
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3* Mayor Bartlett pleading with Sepulcher, his dead son, whom he '''killed''' - before being mercilessly crushed.
4* "She loves dollies..." And the door leading into Scarlet's boss room, with things like "Daddy, I love you" and "I want to die" written in blood on it.
5** Made even more heartbreaking by the fact that her father loved her and spoiled her to make sure she had a happy life before he was forced to murder her. He's so scarred by it that he can't stop cutting himself, and when Scarlet rises as a monster, she cradles him for a moment... before literally biting his head off.
6* Elle's theme at first sounds a little sad, but then you find out what happened to Nora.
7* The scene with Alex and his mother in the prison. It goes from heartbreaking to downright ''traumatizing'' if you decide not to mercy-kill her.
8* Alex forgiving his father in the church is both this and a SugarWiki/{{Heartwarming Moment|s}}. The revelation that he ''did'' love Alex, but tried his best never to show it due to knowing he would have to sacrifice him eventually doesn't help. Neither does him asking Alex to forgive him before being brutally killed by Pyramid Head.
9** Because of the nature of the choice, the player gets the feeling of there being a "good" and "bad" choice, but not a ''right'' choice. Which one is deserved? All of the suffering Alex has endured up to this point comes to a head in this quiet meeting. Either one can produce tears of the appropriate extreme, anger or sadness.
10-->'''Alex:''' If you truly want forgiveness, then you already have it.
11-->'''Alex:''' I promise you, whatever hell awaits you, it won't be long before you see it.
12** Further, Alex's next line, no matter the choice, is the same ("I don't need anything from you."), but the delivery and meaning behind it is completely different. For one choice, the delivery is quiet, as if to say "No, that's alright; you don't need to do this if you don't want to." For the other choice, the delivery is angry, and an outright rejection.
13* The scene with Josh before the final battle. Even if you are anticipating this twist, it's still a shock that a simple unauthorized boat trip in the middle of night led to Josh hitting his head and drowning after going overboard, all because of a petty argument over Alex playing keep away with Josh's family ring.
14-->'''Alex:''' ...No, I can save him. I can save him. He's all right.
15** If you want to take the "Hospital" ending as your preferred canon, then the reason nobody ever reveals that Alex killed Josh is probably because they're all characters of Alex's psyche, and thus involved in the cover-up that forces Alex to journey to the end to remember the truth. Alex is being treated for severe mental distress after his involuntary manslaughter of Josh, and the gameplay can be seen as Alex trying in vain to find his missing brother in his fantasy world.
16* Alex tearfully coming to terms with what he did over a manifestation of Josh's dead body, including giving back his necklace and flashlight to his little brother.
17-->'''Alex:''' I'm sorry, Josh. I never meant for this to happen. Here buddy... take this. I forgot... Josh... I'm sorry...
18* The Bogeyman/Judgement ending can come across as Alex JumpingOffTheSlipperySlope even though Alex's reward of becoming a Pyramid Head isn't what he had in mind. Similar to the sacrificial children, Alex has transformed into a vengeful monster and will presumably terrorize people who have done horrible deeds but it appears VengeanceFeelsEmpty from not forgiving key people near the end of the game. It also overlaps with NightmareFuel as to get this ending, Alex has to let his mother die an agonizing death; this action can be interpreted as Alex panicking at the thought of mercy-killing her or even Alex showing no mercy for the abuse he endured.

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