Season 3 guess
I think that season 3 will start the player off as either Lilly or Christa. It will catch us up on what she has been through, and the changes that have happened to her. I think that her finding Clementine will be similar to when Clem found Kenny, and his group. Time will have went by, and no matter what choice you made at the end of Season 2, she will end up there. She will explain how things went bad with Kenny/Jane/Alone/Wellington. At this point I think Telltale might actually do something they haven't done, and that is switching off to play someone else mid game. I think sometimes we will play as Clementine, going on missions, and then back to Christa/Lilly.
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There's plenty of characters whose fates were left hanging. Lilly, Molly, Christa... I'd really like them to come back in S3.
With them being so liberal with killing people it leaves me to think that they left opening's for certain characters to come back. With Kenny gone I figured Lilly was the most likely to come back because of her strong story in Season 1