Dark Souls/Tear Jerker

"Quelaag? Please, sister, do not cry. I'm happy, truly. I have you, don't I?"
 * Every single line spoken by the Daughter of Chaos is absolutely heart-rending.

"Farewell... my rescuer..."
 * Solaire becoming possessed is bad enough, but is made undeniably worse by the fact that he's become delusional and believes that he's managed to finally find his own personal sun...
 * If the player kill the Giant Blacksmith, his final words are "Nighty-night...".
 * Killing Dusk of Oolacile also prompts a heartbreaking line:


 * Likewise, Siegmeyer's dying words (should the player opt to kill him) have him calling for his daughter. Try not to feel terrible about that.
 * The conclusion to the Siegmeyer and Sieglinde sidequest.
 * An alternate conclusion to the sidequest is no happier.
 * There's a very subtle one involving Witch Beatrice.
 * When you get Great Gray Wolf Sif's HP down far enough, he actually starts limping and his attacks become slower. Given that he's a Punch Clock Villain at worst and one of the most beautifully animated creatures in the game, it's hard to score the final blow. Is it any wonder there are so many rumors stating you can spare him at this stage?
 * Ceaseless Discharge seems like a one-off, gruesome monster that plays no point but to guard Lost Izalith and a decent armor set, set? Well, according to some hints in game and also outright stated in an interview with one of the creators  Bet you feel bad for chuckling at his name now, huh?
 * Logan's fate
 * Several characters you speak to tend to finish conversations with something to the tune of "don't go Hollow". Just a farewell at first, until several of them start Hollowing one by one. How many of their friends did they lose?
 * Crossbreed Priscilla. Particularly, killing Crossbreed Priscilla. She's pretty much the only boss that rather than preemptively striking, politely asks you to leave her alone- even Sif just attacks on sight.
 * Even better: When you go into the Painted World and read up on the lore about a "life stealing abomination", you go in expecting to face a horrible monster that was once one of the greatest enemies of the gods. What you find instead is a depressed, lonely, and terrified young woman whose only "crime" was being born a half-breed, and practically begs you to just go away and leave her alone.
 * The final section of the game deserves a slot here as well. You spend the entire game working up to this moment, ringing the Bells of Awakening, braving the notorious Sens Fortress, traversing the abandoned streets of Anor Londo, and overcoming all other obstacles to open up your final destination. What awaits you here?  Dispatching these final enemies what is there as the final fight in this game? None other than
 * One Youtube comment described it as less an epic boss battle and more an execution of