Set in the present day with flashbacks to the 1990s, the heartwarming and sentimental live-action comedy revolves around outgoing middle schooler Sydney Reynolds who lives with her single dad Max in the house he grew up in, along with her progressive grandmother Judy — three generations under one roof. As Sydney’s preteen pursuits begin to expand with unexpected and funny twists, Max tries to get a better sense of the guidance, perspective and support she needs. Judy lends her wisdom and wisecracks to both granddaughter and son and has a razor-sharp memory that Max’s own teenage antics parallel Sydney’s. Flashback scenes to a young Max and his best friend Leo juxtapose the funny predicaments invented by Sydney and her vivacious friend Olive.