Cleo is eager to return to work after a six-month absence. Tony has to work with his nephew, balancing the roles of agent and uncle.

Tony and Cleo learn the importance of parenting while preparing a party for Nathan’s 16th birthday. Roger is excited that Charlie is named his school’s hall monitor and takes him to work to show him the ropes.

To bond with her father and brother, Victoria joins their improv class. Meanwhile, Cleo helps Nick restore his reputation with the city of Chicago.

Tony accompanies Cleo to a dental conference. Victoria and Nathan go to the movies together, but Victoria is bullied for her cosplay.

Victoria enlists Nathan’s help with her student body presidential campaign. Tony asks for a day alone to honor his his late wife, Joy, but keeps getting interrupted.

The family takes a trip to the mall, where Tony and Nathan are racially profiled in a store. Victoria realizes her own racial prejudices.

Tony and Cleo DIY their kitchen sink. Victoria struggles to work with her team on a group project

Cleo’s father, Harvey, comes to stay with the family after Tony delays his plans to move to a retirement home. With Nick’s guidance, a fragile Roger attempts to rejoin the dating pool.

When Cleo botches a big presentation, she discovers shocking news that will change the family’s life forever. Tony faces his biggest test as Nick’s agent as he renegotiates a new contract for him.

Tony and Cleo plan to celebrate their six-month anniversary, but Tony gets distracted at work. Victoria and Nathan try to outdo each other when buying gifts for their parents.