Jack has a slight problem with Maya's new boyfriend- he's the same age as Jack. When he voices his disapproval to Maya, she accuses him of being hypocritical, since he married someone her age. Both parties are left with a personal dilemma. Jack wonders if he is in fact being hypocritical, and Maya wonders if she may be dating the man to get back at Jack. Meanwhile, Nina's flirtation with a window washer proves hazardous to his health.

At first, Elliott's attempts to warn Finch about dating his ex-girlfriend, supermodel Nikki Elston, seem like just jealousy. However, there's more than a grain of truth in his warnings- Nikki is a true nutcase who delights in putting men through hell. One of her favorite stunts is locking them on a perch in a giant birdcage. Meanwhile, Nina's attempts to get a raise from Jack are subverted by the discovery of the truth about her use of the company's expense accounts.

Jack has two tickets to a London performance of King Lear, but when he is forced to cancel his plans, he is forced to decide who to give the tickets to- the suck-ups Nina and Elliott, who just want the vacation on his private jet, or true Shakespeare die-hard Maya. The adventure that follows parallels the play. Nina and Elliott get the tickets, but their endless conniving against each other proves to be their undoing, while only Maya stays true to her father.