Saddest moment. E V E R

[Ser Eric]

Kevan Lannister in the Epilogue of DwD.

I have children. I have a wife. Oh, Dorna.

[lakin1013]

"Don't look!" a thick voice snarled at her. ... The old man shook her so hard her teeth rattled. Shut your mouth, and close your eyes, boy. ...Look at me. Yes, that's the way of it, at me." [GoT, Bk 1, Arya POV]

Yoren not letting Arya watch them execute her father. I loved Yoren at that moment. And it still brings tears to my eyes. For all the times I have watched the GoT eps, I have NEVER seen them behead Ned because I "don't look!"

[KINGpanther]

TV show having The Fucking Hound lose a brawl to a woman (even if Brienne) because 2014 gender card

That did suck

[GHOSTSTARK]

This from Theon made me sad.

“And Robb. Robb who had been more a brother to Theon than any son born of Balon Greyjoy’s loins. Murdered at the Red Wedding, butchered by the Freys. I should have been with him. Where was I? I should have died with him."

have to agree with this one

[Sullen]

Pretty much all of Theon's material across ACoK and ADwD.

Brienne's discussion with Elder Brother also qualifies.

[Long Live The Onion King]

Arya arriving at the Twins expecting to be reunited with her family only to see the results of the Red Wedding. This after also seeing her father beheaded.

[Ser Frasier of House Crane]

He's definitely one of the worst. I hope he meets a bad end.

Preferably one that has him mewling like a run-over cat in the vicinity of Sam.

[The Onion Sleight]

Sam talking about his father threatening to have him killed if he didn't join the NW always stuck with me.

I can't think of a single character that I dislike more than Randyll Tarly.

I agree so much!... The series has really many, many bad fathers and kids with daddy issues and, unfortunately, these kids often become horrible persons... But Sam's really one of the most caring, nicest, best guys and his father is just the world's greatest SHIT! I hate him so much...

[Galaxian]

1. Ned's death. What really got to me in the moment was Yoren trying to keep Arya from watching.

2. Maester Luwin's death.

3. This one isn't a death and I haven't gotten to it in the books, but the goodbye between Tyrion and Bronn in the TV show.

[Blackfyre Gateau]

So many, too many. For some reason this one always sticks with me:

"Save me the Freys," the Bastard was shouting as the flames roared upwards, "and burn the rest. Burn it, burn it all."

The last thing Theon Greyjoy saw was Smiler, kicking free of the burning stables with his mane ablaze, screaming, rearing...

[Blackfyre Gateau]

'Egg? Egg, I dreamed that I was old.'

For some reason, it breaks my heart every time I read that line.

Same boat. Heart-wrenching...

[The Wolves]

Catelyn begging Ned to make the pain stop, because the cruel world had taken all her babies from her, ~sniff~

Arya saying she had a hole in her heart which nobody let alone a little girl should ever feel

Sansa's depression after Ned died and Tyrion hearing her sobbing behind closed doors about Cat and Robb.

Rickon defending Ned's tomb saying he was coming back to him and him telling Maester Luwin how he can't die.

Jon telling Sam to pull up his hood and remembering Robb and how he didn't know it was the last time he would see him.

Bran in the cave wanting his brothers and sisters and wanting them to learn to fly and live in Maester Luwin's raven rookery

Robb saying Grey Wind as he was murdered.

[Gregor Clegane's head]

Bran seeing his father through the tree.

Theon reunited with his sister.

Winterfell and smiler burning ( hate animal abuse, poor horse. :( )

Old Nan and the rest of Theon and the Starks childhood friends being shipped off to the dreadfort.

Jeyne Poole.

I hope Ramsay burns in hell forever when he dies.

[RavenKing23]

Not really saddest moments ever but I was unexpectedly upset when Quentyn wanted to go visit his mom, just to let her know he hadn't forgotten her. And when Tywin said Robert only used an old hunting knife Jon Arryn gave him and I realuzed that was the knife he used to kill the boar

[Ser Wilfred]

Neds inner monologue in the Black Cells, all his regrets :/

[sj4iy]

When he finally put the quill down, the room was dim and chilly, and he could feel its walls closing in. Perched above the window, the Old Bear’s raven peered down at him with shrewd black eyes. My last friend, Jon thought ruefully. And I had best outlive you, or you’ll eat my face as well. Ghost did not count. Ghost was closer than a friend. Ghost was part of him.
Jon rose and climbed the steps to the narrow bed that had once been Donal Noye’s. This is my lot, he realized as he undressed, from now until the end of my days.

Sam, you sweet fat fool, you played me a cruel jape when you made me lord commander. A lord commander has no friends.

[Blackfyre Gateau]

Just thinking about this more, some of the Arya POV chapters - especially in ACOK, even more so than ASOS, are draining emotionally.

Two passages in particular really stand out:

But Arya would not leave until they found Yoren. They couldn't have killed him, she told herself, he was too hard and tough, and a brother of the Night's Watch besides. She said as much to Gendry as they searched amongst the corpses.

The axe blow that had killed him had split his skull apart, but the great tangled beard could be no one else's, nor the garb, patched and unwashed and so faded that it was more grey than black.

Ser Amory Lorch had given no more thought to burying his own dead than to those he had murdered, and the corpses of the four Lannister men-at-arms were heaped near Yoren's. Arya wondered how many men it had taken to bring him down.

He was going to take me home, she thought as they dug the old man's hole. There were too many dead to bury them all, but Yoren at least must have a grave, Arya had insisted. He was going to bring me safe to Winterfell, he promised. Part of her wanted to cry. The other part wanted to kick him.

- I never cry reading books, but this one did seriously choke me up a fair bit.

Just one other that HAS to be mentioned, because it shows that whatever misfortunes the gods choose to visit on the highborn, those they visit on the smallfolk are always worse:

The Mountain would come into the storehouse after he had broken his fast and pick one of the prisoners for questioning. The village folk would never look at him. Maybe they thought that if they did not notice him, he would not notice them... but he saw them anyway and picked who he liked. There was no place to hide, no tricks to play, no way to be safe.

A smiley old man mended their clothing and babbled about his son, off serving in the gold cloaks at King's Landing. "A king's man he is," he would say, "a good king's man like me, all for Joffrey." He said it so often the other captives began to call him All-for-Joffrey whenever the guards weren't listening. All-for-Joffrey was picked on the fifth day.

[Galaxian]

The Night Watch's eulogies. Just the way the finish it off with: "And now his watch is ended."

[JonCon's Red Beard]

Well, all of those aspects of him, as well as him 'failing Rhaegar' at the battle of the bells and his devotion to Aegon even though he is going to die.

And in the back of my mind realizing: this is all going to be in vain.

Not the saddest moment, but his chapters are heartbreaking. You realise he did nothing wrong and got exiled, his actions caused the man he loved to died and now he has a chance to retake everything, he's going to die either way.

"Death, he knew, but slow. I still have time. A year. Two years. Five. Some stone men live for ten. Time enough to cross the sea, to see Griffin' s Roost again. To end the Usurper' s line for good and all, and put Rhaegar's son upon the Iron Throne.

Then Lord Jon Connington could die content".

[Faint]

Pretty much every time Ned or Robb fucked Catelyn over, with the Red Wedding being the culmination of it all.