Bobby reluctantly accepts the overly-competitive Lowell as his tennis partner for an upcoming tournament. The two are in line to win when two senior members of Bobby's office (Stephen Tobolowsky and George Wyner) blackmail him into throwing the championship match. Meanwhile, to prove to his friends he is not so conservative, Will is talked into texting a photo of his private parts to a girl he has only dated once.

Trying to prove they can drink like Lowell, Bobby and Will go out on the town with him, only to wake up the next morning to the realization that they stole police bicycles sometime during the night. Kate gets upset when a cashier (Jonathan Slavin) gives Jules special treatment, while Andi is upset to discover that Bobby has a former Playboy Playmate of the Year for a client.