Winnie Perry is fourteen now, and the countdown to high school is shaping up to be as eventful as an entire year of middle school. Not only are things shaky with her boyfriend, Lars, but BFFs Dinah and Cinnamon have been acting weird, big sister Sandra is college-bound, little brother Ty has smuggled a stolen penguin home in his backpack, and new baby sister Maggie has everything turned upside down. It's a lot for anyone to handle, and loyal Winnie is so busy worrying about everyone else that she hardly notices that she might just be struggling a little bit herself.