There’s a big walrus-like creature in WoD content that I him-hauled about killing. I /loved, /hugged and /cried when I killed him.
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This and :
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Archaedas, the titan keeper in Uldaman. We broke into his house and killed him way back in Classic. We didn’t know anything about titans or titan keepers back then. Turns out he was a good guy and we just killed him for no reason.
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We didn’t kill Runas the Shamed, but I felt like we didn’t do enough to save him, and watching him transform and wither was sad =(.
Also, the quest chain for Grong felt very, flowers for algernon to me and that was painful for watching him lose his intelligence and than having to kill him later because the horde are jerks lol.
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I felt really bad killing opposite faction NPCs in Silithus at the end of Legion. Legit hadn’t finished brushing the dust of Antorus off my cloak and all of a sudden I’m murdering Horde bc “McGuffin rocks popped out of the ground!” Absolutely hated doing that quest.
Really wanted to just fly off and chill with Khadgar. When he was like “this is stupid and I hate it, peace” it was like he was speaking my mind.
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I like killing in general. And if it’s dramatic and “sad” it’s even better. Fighting last boss in Sekiro was super cool, even though we basically HAD to fight, instead of want it
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Suna Silentstrike. The first time I did that quest, I legitimately cried. Still get a bit teary-eyed.
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People are probably sick of it now, but killing Dranosh was pretty sad. You see Saurfang cry over his dead sons body and it’s prettt depressing.
And now after seeing Saurfang die to Sylvanas while knowing about Dranosh, man…what a tragic life. 
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I had a blast killing Thrall in visions!!!
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No one mentioned Gamon?
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I did this quest for the first time yesterday on my Vulpera. Poor Suna.
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Vael hands down. He went in to stop Nefarion and was defeated, then before he succumbs to the corruption he gives the raid a massive buff which is the only chance we have to defeat him. I always got a little teary when he turns to us and says “Too late, friends” 
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Such a heart tugging questline! Definitely worth the experience. I hope you enjoyed your time in Pandaria on your cute fox!
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Archmage Sol…
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Logged in just to give you this like 
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I actually didn’t like killing Arthas and ending his reign as the Lich King. I wish I could have permanently joined him as a sexy dead troll. The Scourge is a cool faction. I really enjoyed the death knight starting zone for the simple fact I get to actually be part of the scourge for a few quests.
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I will never recover from this.
https://www.wow-freakz.com/img/screenshots/wowhead_336301.jpg
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You actually killed him? You monster!
As for me:
Nazgrim got me good, I downright /saluted him before we engaged the fight in MoP every time
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How do you live with yourself?
Critho the pug puppy in Stormwind. When he first came out there was raid made to kill him and I joined… the only thing he dropped was an empty puppy collar with the text “The saddest thing.”
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