After missing her second birthday party, Jimmy throws 2-year-old Edie a birthday bash at his restaurant to make amends. He also invites Sara's brother, not knowing that Sara told the family that Jimmy left her to raise Gerald. alone.
When Gerald can't make it in time for Edie's interview at the most elite pre-school in the area, Jimmy steps in to help out. But once he meets the admissions counselor, he accidentally starts a lie that takes on a life of its own.
Jimmy hires Gerald as the new host at his restaurant and gives him a crash course in hospitality. Meanwhile, Vanessa teaches Sara how to take sexy photos for Bruce, and Annelise encourages Ravi to crack down on the comedy in the kitchen.
When Sara and Gerald learn Jimmy hasn't been to a doctor in more than a decade, they trick him into seeing theirs; Gerald and Vanessa fret over Edie's surgery; Annelise and Ravi discover Jimmy's secret.
In an effort to prove that he doesn't always need validation from women, Jimmy spends an evening at a Korean spa with Ravi, Gerald and a few guys from the restaurant. Meanwhile, Sara, Vanessa and Annelise go out for a girls' night at the hottest new bar in Los Angeles.
When Sara invites Jimmy to accompany her to an ex's party and play the role of her boyfriend, Jimmy realizes his feelings for Sara may be deeper than he thought. At home, Gerald and Vanessa panic about their parenting abilities when Edie starts acting out.
When Jimmy has trouble admitting that he's 51, he throws himself a second 50th birthday party. The party triggers flashbacks of where he was a year ago, showing Jimmy what a difference his family has made in his life.
Jimmy and Sara wonder if they should give their relationship another shot, but Sara is hesitant to put herself in a position to get hurt again. Meanwhile, Gerald plans an elaborate proposal for Vanessa.