Set in the present day with flashbacks to the 1990s, life revolves around outgoing middle schooler Sydney Reynolds who lives with her single dad, Max, and progressive grandmother, Judy – three generations under one roof! As Sydney navigates the unexpected and even “catastrophic” challenges of being a preteen, Max is desperate to get a sense of the guidance, perspective and support she needs. Grandma, full of both parental wisdom and wisecracks, uses her razor-sharp memory to prove that Max's own teenage antics often parallel Sydney's.