Regina Calloway is having trouble adjusting to adulthood. Her younger, more successful sister Katherine, just got engaged, her younger brother is graduating from high school and has been accepted to one of the nation's best art programs, and she's stuck in a job she doesn't like, which doesn't fit into her mother's high expectations of her. She's finally met a decent guy, but while trying to navigate the waters of a new relationship, a former classmate tries to torpedo the new couple before they can set sail. Regina has to compete with over-achieving siblings, avoid her mother's constant interrogations, learn how to be in a relationship and figure out what she want's to do with her life, all while being forced to join her family every weekend for margaritas. Will Regina be able to blossom into adulthood, or will she remain at a post-adolescent standstill, watching everyone around her become the adults she can only hope to be?