Exuberant dreamer Ben Fox (Nat Faxon) returns to his hometown and reunites with his younger sister Kate (Dakota Johnson), an overly responsible single mom raising her five-year-old daughter, Maddie (Maggie Elizabeth Jones). But when he arrives, he finds a sad state of affairs. For the first time in their lives, Kate needs Ben's help, and he's determined to bring some much-needed chaos into her stable world. In the series premiere, Kate enlists co-worker BJ (Lucy Punch) to help her prepare for what turns out to be a disastrous first date, while Ben teams up with childhood pal Tommy (Echo Kellum) to stop an ex from getting married.