When Maya's first love John Kenny pops back into town, she becomes as happy as she's ever been, as the two find their old spark back in full force. However, Jack is angry about the whole thing, as he still has not forgotten when he walked in on the two of them fooling around one time. Maya then learns the true horror of the situation- the only reason they were separated in the first place was because Jack had pulled strings to get him into the Royal Shakespeare Company, and she becomes instantly fearful that he will once again begin to interfere with their relationship. Meanwhile, Finch uses a ""tough love"" method to train a new intern while Nina's television appearance is ruined when an old allergy acts up.

Maya becomes smitten with a United States Senator, but loses him to Nina through a series of deceptions on Nina's part. Nina convinces him that she is an old-fashioned Southern belle with no vices whatsoever, and that Maya is a drug addict. Also, when it is revealed that Elliott stole a Six Million Dollar Man doll as a kid, he becomes racked with guilt over it while Finch can only think of the potential collector's value of the item. Finally, Jack decides to see what life is like from his employees' point of view and moves his desk into the center of the office.