When Jimmy realizes that he doesn't know much about Gerald, he decides to take him out for a night on the town. Meanwhile, Annelise hires a new mixologist to spice things up at the restaurant.

After Jimmy misses Edie's second birthday party, he decides to throw her a big bash at his restaurant to make it up to the family. When Sara's brother shows up, he brings the party to a screeching halt by confronting Jimmy about leaving Sara to raise Gerald on her own.

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.

In a quest to find his own Amal Clooney, Jimmy goes out with Sara's co-worker, but when she is not impressed with his smooth moves, Jimmy turns to Sara for pointers. Meanwhile, Gerald and Vanessa decide to become friends with benefits.

In hopes of helping Gerald score with the ladies, Jimmy takes him out for a swanky night on the town. But when Gerald falls for a party girl, Jimmy fears she may be into Gerald for the wrong reasons. Meanwhile, Vanessa starts a mentorship with Annelise.

Jimmy plans his annual Malibu Thanksgiving day with one of the hottest stomach models on Instagram, but his plans get derailed when he swings by Sara's house for an obligatory holiday visit and feels threatened by the return of her ex-boyfriend, Bruce.

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.

After hearing that Jimmy hasn’t been to the doctor in more than 10 years, Sara and Gerald trick him into seeing their family doctor for a routine physical, which results in an unsettling discovery. Meanwhile, Gerald and Vanessa stress over Edie’s upcoming surgery, and Annelise and Ravi stumble upon Jimmy’s secret safe.

When Jimmy reunites with his old buddies in the "Sat Pack," Ronnie gives him a hard time about his new life as a family man. Meanwhile, Bruce springs big news on Sara, and Gerald is blindsided by Frankie's confession.

Vanessa and Jimmy get Edie involved in baby modeling - without Gerald or Sara finding out. Meanwhile, at the restaurant, Annelise loses her composure when she falls for a restaurant staff member.

In an effort to beef up the cool factor of his restaurant, Jimmy throws a party for Chason Fairwick - one of the biggest pop stars around - which includes decking out his restaurant in full '80's garb. Meanwhile, Ravi believes the secret to boosting reservations lays in tableside guacamole.

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 Edie is bitten at school, Jimmy and Sara go to great lengths to find out who did it. Meanwhile, Ravi sets up a meeting for Gerald and Vanessa to meet a flashy tech investor named Kirk, but once they meet him, they are not so sure they’d like to do business with him.

Jimmy attempts to protect Gerald from an Internet bully. Sara and Vanessa decide to visit the bully's mother but things get worse.

After Sara asks Jimmy to pose as her boyfriend at her former boyfriend's party, Jimmy realizes he still has feelings for her. Gerald and Vanessa have some doubts their parenting skills after Edie starts to be have badly.

Jimmy ends up feeling out of his depth after he falls for a stunning chief executive officer who is always one step ahead of him.

Jimmy attempts to deal with the realities of being in a relationship. Vanessa and Gerald attempt to balance their lives and their jobs at the same time.

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 plans an emotional memorial service while processing a painful loss. Meanwhile, Sara is faced with a difficult decision after Craig asks her to take the next step in their relationship.

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.