Darkest moment in the series

[Lord Greenhood]

Question is open to interpretation, whether humorous or seriously fucked up etc...

I have two that hit me.

Theon dreaming of the two miller boys (One of which is likely his son) he killed.

Last night he had dreamed himself back in the mill again, on his knees dressing the dead. Their limbs were already stiffening, so they seemed to resist sullenly as he fumbled at them with half-frozen fingers, tugging up breeches and knotting laces, yanking fur-trimmed boots over hard unbending feet, buckling a studded leather belt around
a waist no bigger than the span of his hands. “This was never what I wanted,” he told them as he worked. “They gave me no choice.” The corpses made no answer, but only grew colder and heavier.

Tyrion

He did not sleep at all that night.
Instead he lay in the dark, staring up at the canopy and counting his ghosts. He saw Tysha smiling as she kissed him, saw Sansa naked and shivering in fear. He saw Joffrey clawing his throat, the blood running down his neck as his face turned black. He saw Cersei’s eyes, Bronn’s wolfish smile, Shae’s wicked grin. Even thought of Shae could not arouse him. He fondled himself, thinking that perhaps if he woke his cock and satisfied it, he might rest more easily afterward, but it was no good.

Was Tyrion jerking off to all of those mental images? If so, not sure if funny or just dark. 

[Maester of Valyria]

I always give this quote whenever a topic like this starts:

Jeyne pulled her wolfskins up to her chin. "No. This is some trick. It's him, it's my … my lord, my sweet lord, he sent you, this is just some test to make sure that I love him. I do, I do, I love him more than anything." A tear ran down her cheek. "Tell him, you tell him. I'll do what he wants … whatever he wants … with him or … or with the dog or … please … he doesn't need to cut my feet off, I won't try to run away, not ever, I'll give him sons, I swear it, I swear it …"

It's lines like that that make you fear for the mind of the man who wrote them.

 

Or, if we're not confined to the main five books:

The last living offspring of Aegon II, Jaehaera Targaryen was eight when she wed her cousin Aegon III, and ten when she threw herself from Maegor's Holdfast to the spikes of the dry moat below. She lived on for half an hour, in agony, before she died.

[Nissa]

1 hour ago, Maester of Valyria said:

I always give this quote whenever a topic like this starts:

Jeyne pulled her wolfskins up to her chin. "No. This is some trick. It's him, it's my … my lord, my sweet lord, he sent you, this is just some test to make sure that I love him. I do, I do, I love him more than anything." A tear ran down her cheek. "Tell him, you tell him. I'll do what he wants … whatever he wants … with him or … or with the dog or … please … he doesn't need to cut my feet off, I won't try to run away, not ever, I'll give him sons, I swear it, I swear it …"

It's lines like that that make you fear for the mind of the man who wrote them.

First thing I thought of when I saw the topic. 

[YOVMO]

2 hours ago, Maester of Valyria said:

I always give this quote whenever a topic like this starts:

Jeyne pulled her wolfskins up to her chin. "No. This is some trick. It's him, it's my … my lord, my sweet lord, he sent you, this is just some test to make sure that I love him. I do, I do, I love him more than anything." A tear ran down her cheek. "Tell him, you tell him. I'll do what he wants … whatever he wants … with him or … or with the dog or … please … he doesn't need to cut my feet off, I won't try to run away, not ever, I'll give him sons, I swear it, I swear it …"

It's lines like that that make you fear for the mind of the man who wrote them.

 

Or, if we're not confined to the main five books:

The last living offspring of Aegon II, Jaehaera Targaryen was eight when she wed her cousin Aegon III, and ten when she threw herself from Maegor's Holdfast to the spikes of the dry moat below. She lived on for half an hour, in agony, before she died.

Second. This one will be hard to top