After breaking up with her boyfriend and being sexually harassed at a bar, Maya Carter has had enough. One day at a company costume party, Maya is costume as Gene Kelly for Singing in the Rain and Maya feels a certain change, a comfortable change. Maya decides to have a sex change and becomes Mason. After that, she gets an unexpected visit from her parents (Keaton and Steenburgen) and she reveal her new identity to them, leaving them skeptic. They tell her that her sister (Brie) is getting married and she's invited to be her maid-of-honor. What follows is a series of awkward and discriminative events that lead into the wedding.