The trailer for Game of Thrones season 8 already teased this awkward meeting. Apparently, According to reliable sources, the first scene of Game of Thrones season 8 will take place in the winter town, a village situated right outside of Winterfell. The town has apparently been shown on the show a few times. Reportedly Brienne and Podrick stayed there in season 5 while waiting for Sansa to light a candle in the broken tower, and Tyrion visited a brothel there in the very first episode of the series.
As for what will happen in the winter town, Entertainment Weekly's James Hibberd gives us some hints in his huge cover story about the final season:
Season 8 opens at Winterfell with an episode that contains plenty of callbacks to the show's pilot. It is being reported that instead of King Robert's procession arriving, it's Daenerys and her army. What follows is a thrilling and tense intermingling of characters — some of whom have never previously met, many who have messy histories — as they all prepare to face the inevitable invasion of the Army of the Dead.
Hibberd confirms that this is what it looks like: Sansa is hugging Jon Snow hello, but looking over his shoulder suspiciously at Daenerys Targaryen, the strange new ruler he's brought to Winterfell. Emilia Clarke, who plays Daenerys, has said she'll share scenes with both Sophie Turner (Sansa) and Maisie Williams (Arya), which should be a blast. And Hannah Murray (Gilly) has said that she has a few new interactions with cast members that she's excited about.
The final season may have many more callbacks to the past seasons of the show and many more shocking twists yet to deliver. We can hardly wait.