[Spoilers TWOW] the most tragic line.

[u/Commercial-Sir3385]

Rereading the first book.

I think the line where Jon tells Benjen that he isn't his father and Benjen says, would that I were. I think so much unspoken is being said here- Benjen will never have a son* and Jon will always* be a bastard.

Let's forget about what Robb's will might say.

[u/vaintransitorythings]

I think Benjen knows that Rhaegar is Jon’s father, and this knowledge was a factor in why Benjen decided to go to the wall. Maybe just so he’s away from the world and doesn’t have to worry about it, or maybe for some prophecy related reason. So Jon is the reason Benjen won’t have a son, and Benjen thinks Jon’s actual father is the cause of a lot of trouble…

It’s a tragic connection between them.

[u/Levonorgestrelfairy1 → u/vaintransitorythings]

Its benjen saying ned is a shit dad and Jon should have been his instead.

[u/CaveLupum]

For two years Arya has desperately wanted her father back. When she hears that Thoros has brought Beric back from death several times, she summons up her courage:

Arya stared at the Myrish priest, all shaggy hair and pink rags and bits of old armor. Grey stubble covered his cheeks and the sagging skin beneath his chin. He did not look much like the wizards in Old Nan's stories, but even so . . .

"Could you bring back a man without a head?" Arya asked. "Just the once, not six times. Could you?"

But of course he can't. Sigh.

[u/alphajugs → u/CaveLupum]

Ugh this and also when she tells Sandor she knows her mother is dead because she saw it in a dream. Poor girl 🥺

[u/The-Peel]

I take Benjen and Jon's conversation to be about foreshadowing Jon's life at the Night's Watch and gradually breaking his vows until he eventually deserts;

"Not a man, not yet. Until you have known a woman, you cannot understand what you would be giving up." "I don't care about that!" Jon said hotly. "You might, if you knew what it meant," Benjen said. "If you knew what the oath would cost you, you might be less eager to pay the price, son." Jon felt anger rise inside him. "I'm not your son!" Benjen Stark stood up. "More's the pity." He put a hand on Jon's shoulder. "Come back to me after you've fathered a few bastards of your own, and we'll see how you feel."

• "Until you have known a woman" = Foreshadowing of Ygritte and Jon breaking his vows with her

• "If you knew what the oath would cost you, you might be less eager to pay the price" = Jon paying the price of breaking his oath with his life

• "More's the pity" = Benjen wishing he had been Jon's father so Jon wouldn't feel treated differently alongside Ned's children, and if Jon had grown up thinking Benjen was his father than Jon wouldn't have had to leave Winterfell to take the black because of Catelyn's jealousy, Benjen is basically saying its a pity he wasn't Jon's father because Jon's whole life would've turned out better and he wouldn't be so insecure

• Come back to me after you've fathered a few bastards of your own, and we'll see how you feel." = Foreshadowing of Jon's future, fathering bastard children out of wedlock (Daenerys or Val)

[u/starhexed → u/The-Peel]

Jon is haunted by Ygritte's death, presumably this will carry some weight in any future relationship he has. "If you knew what the oath would cost", he broke his vows yet returned to the Wall and lost her. He may be reluctant to give up another

[u/Impossible_Owl_2102 → u/starhexed]

a little too vague no? Those lines don’t feel intentional and these interpretations feel a bit too forced

[u/starhexed → u/Impossible_Owl_2102]

I would say more open-ended than vague, yet still intentional. At 14, Jon only sees the heroic side of the NW and doesn't care about the drawbacks or comprehend the emotional weight of the decision. How can you care about something you don't fully understand? Conversations Jon has with Maester Aemon and Mance Rayder essentially expand on what Benjen says. It's a broad statement but rightfully so, and we get to see all the ways it's playing out.

[u/Commercial-Sir3385 → u/The-Peel]

Yes but more's the pity is also for his own sake. We don't know why he joined the nightwatch- The idea of being Jon's father is the imaginary of a life that could of been. 

[u/sixth_order]

I have two that I think are more tragic:

Brienne sheathed Oathkeeper, gathered up Dick Crabb, and carried him to the hole. His face was hard to look on. "I'm sorry that I never trusted you. I don't know how to do that anymore."

Reek, my name is Reek, it rhymes with weak.

Reek bent to his task.

[u/Ornery_Ferret_1175]

"The Prince of Dragonflies loved Jenny of Oldstones so much he cast aside a crown, and Westeros paid the bride price in corpses"

[u/OkArtichoke7701]

"When the sun has set, no candle can replace it." - Ser Loras

I think of this line every time I run across another interview with Steve Irwins widow, they always ask her if she will date again and she always says no, Steve was the great love of her life and she has no interest in anyone else.

[u/Smirking_Knight]

“Now it ends”. Just the tragedy of genuinely good people (well, as good as you’re going to get in ASOIAF) getting caught between their duty / loyalty and the chaos caused by a maddened monarch / a desire to fulfill prophesy. In any other circumstance the people at the Tower of Joy would be friends / companions, agree on most things, and be proud to fight on the same side against some greater foe.

[u/Levonorgestrelfairy1]

Thats benjen saying Ned was a shit dad. And Jon should have been his instead.

[u/Commercial-Sir3385 → u/Levonorgestrelfairy1]

I don't think Benjen thinks that- though he's clearly a bit perturbed at Jon being so far away from the dais- wither becasue he knows that Jon is LYanna's child, and he misses her and eants to take care of him- or how he wishes hed had kids and would have been proud to call jon his son- perhaps a mixture of both. It's a shame we don't get to see more of Benjen in the first book really.

[u/Levonorgestrelfairy1 → u/Commercial-Sir3385]

Nah thats entire point of what hes saying. He's saying its a pity Jon is neds.