*SPOILER ALERT FOR THOSE WHO HAVE NOT READ ALL OF THE BOOKS*
*TW: VIOLENCE, SEXUAL ASSAULT*
Whenever someone asks me who has the most sorrowful story in Westeros, I always respond with Jeyne Poole. Most people are taken aback, I'm covered in tattoos dedicated to House Stark. Surely I would think that Robb, or that Sansa, has suffered the most? That is not the case. Whenever I think about Jeyne, my heart breaks.
Jeyne's life prior to going to King's landing was benign. Being the only daughter of the Steward of Winterfell, Vayon Poole, which a position that allowed Vayon to have some influence. In Chapter 22 of "A Game of Thrones," it's noted that Ned reserved one place at his table so that he could invite a different servant to join him during the meal. When Vayon sat there, they would talk about money, stores, etc. Although Jeyne wasn't truly of noble birth (which, as we can see, is a detriment to her later), at Winterfell, she's allowed to be schooled with Sansa, and Arya. They did needlework, and learned other becoming lessons that were typical to young ladies at the time. Undoubtedly, the same songs and stories that filled Sansa's head were also filling Jeyne's (it is evident that they were close), so Jeyne probably too dreamt of a Knight, (she was infatuated with Beric Donadarrion at the Tourney of The Hand) or good marriage, one day. Because of this, it can be said that Jeyne knew the repercussions that would occur if she lost her maidenhead prior to then.
Jeyne travels south with her father and several other members of the Stark Household, and subsequently survives the initial massacre there. Not knowing her Father's fate, (he was slain) she is originally imprisoned with Sansa Stark, and cries hysterically for her Father. In Chapter 51 of "A Game of Thrones," Sansa is summoned to the small council, and inquires about Vayon for her friend. Sansa doesn't receive an answer- instead, Cersei demands that Jeyne be separated from Sansa, and that Petyr Baelish should find new accommodations for Jeyne.
Because Jeyne is not of noble birth, she's taken from her friend, and is thrown into working in Littlefinger's brothels.
Jeyne vanishes from the story until A Storm of Swords, when Jamie Lannister is travelling between Harrenhal and King's Landing. When she reappears, it's under the guise of "Arya Stark." Jamie notes:
"When she saw him, she inclined her head. 'Ser Jaime,' she said in a thin, anxious voice. 'You are kind to see me off.'
Jaime studied her closely. 'You know me, then?'
She bit her lip. 'You may not recall, as I was littler then…but I had the honor to meet you at Winterfell when King Robert came to visist my father Lord Eddard.' She lowered her big brown eyes and mumbled, 'I'm Arya Stark.'
Jaime had never paid much attention to Arya Stark, but it seemed to him that this girl was older…"
— A Storm of Swords, page 820
Informing Brienne of Tarth that this girl wasn't the true Arya, (incase Brienne wanted to rescue her) Jamie tells her it's some Northern girl that Tywin found. (We all know that Littlefinger has had Jeyne working in the brothels all along). They dress her up (wolf brooch and all) and ship her North, to have her marry Ramsay Bolton...who could arguably be the most deranged psychopath in the entire series. Ramsay hunts packs of naked women with feral dogs, and names dogs after his favorite captives that he's raped and killed. He flays people alive. A legitimized bastard (something that his Father, Roose, rarely lets him forget), Roose delights in torturing people. The Lannister's don't care. They want to assure the claim on Winterfell.
So, off Jenye goes. What the Bolton's or the Lannister's don't realize, is that a certain someone recognize's this farce: Reek (Theon).
"That is not Lord Eddard's daughter. Arya had her father's eyes, the grey eyes of the Starks....That's Sansa's little friend, the steward's girl. Jeyne, that was her name. Jeyne Poole."
-A Dance With Dragons, page 309.
After Stannis drives the Ironborn out of the Deepwood Motte, the location of the wedding is moved from Barrowton to Winterfell, to goad Stannis into invading, and to strengthen the Bolton's claim.
Jeyne is terrified. Because "Arya" has no one to give her away at the wedding, it is now up to Theon to do so. Jeyne begs Theon to take her away.
"'Help me.' She clutched at him. 'Please. I used to watch you in the yard, playing with your swords. You were so handsome.' She squeezed his arm. 'If we ran away, I could be your wife, or your...your whore...whatever you wanted. You could be my man.'"
-A Dance With Dragons, page 550
Theon advises her to please Ramsay (although acknowledging that Jeyne's name rhymes with pain), and fears that because of Jeyne's brown eyes (that should be grey) her secret might get out. More morbidly, he muses:
"Pretty white teeth, he thought, but if she angers him, they will not be pretty long."
-A Dance With Dragons, page 551
Instead of crowing out the crowd that this was all a farce, Jeyne says her vows. Her eyes are described many times as being full of fear. This wedding also has the distinction of being the one where the guests were fed Frey Pies by Wyman Manderly.
Reek (although he heard his name, Theon, called in the Godswood), is escorted to the bedding chamber. Forced to cut of Jeyne's gown, and small clothes, Jeyne is subjected to humiliation, the reveal of the scars from whipping on her back and the beginning of a sexual assault, before she can utter that she was "trained." (page 567, ADWD) She is then orally assaulted by Reek, prior to Ramsay bedding her.
She is then known only by those at Winterfell by the bruises on her body, and her sobs echoing through the castle.
After a rescue attempt by Mance Rayder, and 6 spearwives, (resulting in the death of the spearwives, and Mance being caged outside, with only their flayed skins for warmth) Theon and Jeyne escape to Stannis' camp. The most heartbreaking moment in Jeyne's story includes during this chapter (51, ADWD), in which it's heavily implied that Ramsay had her copulate with a dog. Jeyne, confused and terrified, thinks that this rescue attempt is some kind of trick.
"'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...or 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...'"
-A Dance With Dragons, page 768.
In a previously released Winds Of Winter Chapter, Jeyne also is inflicted with frostbite while fleeing Winterfell, and upon arriving to Stannis' camp, was informed that she will have to lose part of her nose because of it. Theon reminds her to be "Arya"- if she isn't, she will be only a whore. Which is devestating to read. She is then sent to the Wall, to reunite with her "brother," Jon Snow.
Jeyne's story is undoubtedly the most heartbreaking in Westeros, when not taking into account the horrors that the smallfolk have gone through. Jeyne was a sweet summer child, with a head full of songs and stories, who lost her Father, her only friend, her virtue, and potentially her sanity. The brutality that she faced under both the hands of Littlefinger (her back being riddled with scars) and Ramsay (bruises, abuse, rape) is arguably the worst in the series. Arguably, because Cersei gave her to Littlefinger, and Jamie sent her North, the Lannisters have some blood on their hands as well.
My heart bleeds for Jeyne, and my only hope is that Jeyne finds some solace. I know that because the author of this series is George RR Martin, that may not be the case. Regardless, readers (and viewers) of the series have always mourned for the dead. Don't pity the dead. Pity the living, like Jeyne Poole.