Honestly, I can watch an entire episode of Jon & Sansa just catching up, shooting the breeze, but since "Book of the Stranger" has to update us on what other characters are doing (*sigh* I suppose...), here's the stuff they must've discussed.
  1. Sansa: Arya is alive, still not dressed as a girl.
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    Since Jon & Arya are the closest, Jon would've wanted to hear about her. Imagine the smile on his face. You're welcome.
  2. Jon: I was stabbed to death by my men & then resurrected by the other redheaded woman in this joint. She thinks I'm the chosen one.
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    Sansa is getting a crash course in the magical plot line & this Lord of Light stuff.
  3. Jon: White walkers are real & they are coming to the Wall. Good news is, Valyrian steel & dragon glass can kill them.
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    More crash course on magic for Sansa. Wonder if she knows that Brienne is carrying a Valyrian steel sword that was formerly Ice.
  4. Sansa: Theon didn't really kill Bran & Rickon. Oh, & Theon (now called Reek since castrated & broken by Ramsay) helped me escape, so go easy on him next time you see him.
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    They both know that Bran is the legitimate heir of Winterfell, though neither knows that he's communing with trees.
  5. Sansa: Ramsay raped me repeatedly. Help make me a widow.
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    I'm pretty sure Sansa told him.
  6. Sansa: I was married to Tyrion Lannister, but since he was gentleman enough (& in love with my lady-in-waiting), we never consummated it & that marriage was conveniently annulled.
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    She would probably mention that Pod, Brienne's squire, was Tyrion's as well. And Jon should remember Tyrion somewhat fondly, I'd imagine.
  7. Jon: Speaking of marriage, I broke my vows & almost ran away with this wildling girl, who was killed by the boy who eventually stabbed me in the heart as well. She was "kissed by fire" (meaning: redheads), which is kinda like you, Sansa, & the magic woman who brought me back from the dead.
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    Out of the three women currently in Castle Black, two are redheads. Huh. And don't forget Tormund as well, I guess! Jon likes to surround himself with fire ;-).
  8. Sansa: Speaking of fire, I met this old flame of my mom who is now, like, obsessed with me. He killed that shithead Joffrey for me (got me out of King's Landing) & then his own wife (cause she caught him kissing me) before giving me to fucking Ramsay. I'm angry at him, but he also has the Vale (the most rested army in the 7 Kingdoms) so raven him?
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    Okay, not sure if Sansa will tell Jon everything about Littlefinger, but the fact that he has the Vale army should come up, considering they'll need troops.
  9. Sansa: Lady is dead, but Arya set Nymeria loose somewhere in the Riverlands. Ecstatic to see Ghost is still alive!
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    Where's my Sansa/Ghost reunion, show? I wants it...
  10. Sansa: They beheaded Father, cut Mother's throat, stabbed our pregnant sister-in-law in the stomach, & sewed Grey Wind's head to Robb's corpse. We, as the head of House Stark, need to take vengeance!
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    Okay, I'm not sure if either Sansa & Jon know these details, but if they did, they would've discussed it.
  11. Sansa: How's uncle Benjen?
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    Jon: ...
  12. Jon & Sansa: random reminiscing about their childhood & Winterfell... Old Nan, Ser Roderick Cassell, Jeyne Poole, Jory, Hodor, etc.
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    I cry.