Four months after daughter Henley Grace was born, Jamie and Doug are learning to juggle parenthood with their busy schedules. When Doug’s parents can’t babysit for Henley while the couple is at work, Doug is forced to stay home, threatening his new job. Needing to find an alternative, Jamie suggests daycare, but Doug refuses, leaving them with little to no options for who can watch Henley.

Jamie and Doug prepare to take daughter Henley on her first road trip to visit Jamie’s sisters. But when Jamie’s mom makes a request to meet Henley for the first time, Jamie grapples with how much of a relationship she wants her mom to have with Henley. Later, Doug struggles to babysit four kids at once, and Jamie is blindsided when her sister surprises her with a serious question.

Jamie and Doug are finally ready to redecorate their new home, but their design dreams come crashing down when they get a reality check from their financial advisor. While planning Henley’s future, Jamie and Doug are forced to face their own mortality as they struggle to agree on a guardian for their daughter.

Sensing that Jamie is feeling over worked, Doug plans a full week of surprises, including a visitor from both their pasts. Jamie takes her obsession of making sure Henley is dressed like a girl to a new level when she decides to get Henley’s ears pierced.