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Tear Jerker: Silent Hill 3
The scene where Heather discovers Harry dead, as well as the scene where she laments because she never got to tell him how much she loved him.
Heather: Dad. You used to tell me that you were the strongest man in the world...
Also in the scene before the ending, when she breaks down in tears while thinking of Harry after defeating the final boss.
Also one for the player if they played the first game. Harry, who the player spent the entire first game with, watching as this man put himself through a literal hell to save his daughter, is dead. And he's not coming back. This troper spent a while just sitting staring into space thinking about Harry, and that we'll never see him again.
Douglas' recollection of his son's death.
Douglas: "You..remind me of my son..."
Heather: "I thought you said nobody was going to cry over you."
Douglas: "Dead people don't cry."
For reasons this troper really doesn't want to go into, this exchange has her breaking down into tears every time she plays the game:
Heather: You think you're Superman or something?
Douglas: You know...I always wanted to be him.
And most of these scenes also feature sad music, which makes it all the more tear-jerking.