Most Heartbreaking Moment

[BloodRider]

For me the part that really breaks my heart is when Tyrion lies to Jamie about killing Joff. Gets me EVERY time. Stupid arrogant Tyrion.

[Prince Bran]

Though I'm probably the only one, Luwin's death gets to me.

[Arbor Gold]

Sansa building Winterfell in the snow.

[Jon Targaryen]

I am coming for you Lady Sansa, she thought as she rode into darkness. Be not afraid. I shall not rest until I've found you.

and

Seven, Brienne thought again, despairing. She had no chance against seven, she knew. No chance, and no choice.

She stepped out into the rain, Oathkeeper in hand. "Leave her be. If you want to rape someone, try me."

Brienne is so awesome.

[Millardkillmoore]

It has to be Theon's last chapter in ACOK. His mounting desperation and gradual realization that he as been abandoned to die, utterly alone and utterly unloved (even by his own family) were just unimaginably sad. Plus, Rodrik and Luwin dying.

[Pinely]

It's hard to think of one particular heartbreaking moment being the most, as this series contains so many. There are so many that, every time I come up with one that I think was the worst, there's another one lurking around in my head. Jory, Ned, Dany, Jeor, Jorah, Ygritte, Cat, Robb, Renly, Robert, Davos, etc . . .

Right now, I'm leaning towards King Robert's death. I like Robert a lot, partially because he reminds me of my father. And, he admits all the ways that he had gone wrong. Whenever I read this scene now, I think back to Robert at Winterfell, when he fantasizes about running off with Ned and becoming a Hedge Knight. Plus, there's what happens after his death that makes this event particularly tragic to me.

[talkstoangels]

again, jaime's confession to tyrion. you can practically hear the poor guy's heart shatter

and sansa/tyrion's wedding night. i still find that chapter too painful to read, and it's true testimony to the awesomeness of GRRM when he can write sansa's response to a situation and a character that she just doesn't get, and have the audience completely understand how deeply her words and actions cut tyrion

"I know i am ugly"

"no, my lord..."

"don't lie, sansa" ...*sob*

[DomDayne]

Ditto about Tyrion's lie to Jaime, and Sansa's Winterfell. But, I also found the killing of Lady unbearable, especially so early on in the books, before we knew what to expect from Martin.

[Matarreyes]

Stange, I got into this topic just to see people´s responses, and finished adding my vote to the Tyrion/Jaime reunion-parting scene. Jaime is easily the only person in the world who both genuinely respects Tyrion and cares for him, it´s beyond sad that everything would go so spectacularly wrong that his would be the hand to push Tyrion completely over the edge.

[gollum]

and sansa/tyrion's wedding night. i still find that chapter too painful to read, and it's true testimony to the awesomeness of GRRM when he can write sansa's response to a situation and a character that she just doesn't get, and have the audience completely understand how deeply her words and actions cut tyrion

"I know i am ugly"

"no, my lord..."

"don't lie, sansa" ...*sob*

I find that chapter painful to read as well but for a very different reason. I empathize with Sansa in that situation and not Tyrion. I can imagine how awful it must be to be a twelve year old married against her will to an ugly dwarf whose family killed her father, and it makes me really happy to be living in twenty-first century America.

[stannis for king]

dany exiling ser jorah was a bit difficult to swallow, though i suspect we havnt seen the last of him....

[gollum]

The most heartbreaking moments for me are:

1. Sansa being happy to marry Willas and then being forced to marry Tyrion instead.

2. Arya thinking Catelyn might not want her back because she's dirty.

3. Bran finding Rickon in the crypt right before they get word about Ned's death.

4. Robb's murder.

I hate when bad things happen to the Stark kids. This series makes me miserable, I keep reading to see if things will finally turn around.

[Silverstar]

Red Wedding is easily the most heartbreaking moment for me. Being in Catelyn's head as she watches Robb's murder, and feeling her go insane before they kill her.

Ouch.

[Dreadwolf]

Not something very special and I am not sure why but the Blackfish proudly flying the Direwolf's flag over the Riverun Doomed Castle after RW impressed me deeply.

[Fox And Hound]

There are several, but I cry easily.

The one that sticks out the most is when Cat finds out that Winterfell has fallen and her sons are dead.

Davos, when he is alone and dying and thinking about his sons who died in the flames.

Also, the Red Wedding, the part where Tyrion tells Jaime that he killed Joff, when Sansa marries Tyrion (for both of them), when Ned is executed, when Brienne etc.

If there's a sad part, you can count on me crying...

[hotpocket2006]

Many parts of the books made me cry, most memorably:

Ned Starks death

Sansa's wedding, I epathize with both of them

Dany, sacraficing her baby only to still lose Drago

The Red Wedding and then when Arya shows up and wants to find her mom

When Catelyn thinks her sons are dead

Jon finds Ygritte dead

[ieiazel]

Killing Robb really broke my heart, and it still does every time I think of it.

After that, I guess Drogo's death. I didn't care much about him, but when he died and Dany took care of his dead body... well, it was painful to read.

Also, when Brienne is looking for Sansa and he finds septon Meribald(?), and he explains his views on the broken men. Wow, it is a beautiful and heartbreaking piece of literature

[Silverius]

Arya meeting Harwin at the inn.

[Circle Breaker]

Aemon dying. I thought for sure he'd get to meet Dany at some point. Seems like such a waste.

[Demonic Weasel]

Cressen. Cressen is such a masterfully written POV and he tears me up every time. The texture that he adds on the brothers Baratheon only makes it more poignant.