Shadows is about half done, but I'm gonna sleep on the dialogue a little bit. I wanna find the right blend of conversation and a lack of want to get into some heavy topics, such as Sakura's apparent lack of other friends lol. Shikamaru lacks close friends too, but I think it's not a conversation he'll want to get into since it's never really bothered him much. I may stick to the shogi discussion and get into her training with Tsunade a bit.  At the end of Part 1 of Naruto, Shikamaru also resolved to become a better leader. Maybe she could ask him a little about the Rescue Sasuke mission, maybe not right this second, but eventually. All she knows is that they didn't get the guy back.