Will reveals to his friends – the happily married Bobby and Andi, still-single Kate, and sexy couple Jules and Lowell – that he and his wife (Smith Cho) have finalized their divorce. Soon after, Jules and Lowell announce their engagement, which upsets Kate. Kate's friends then try to get her to be less picky when it comes to men.

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.