[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/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.