Claude takes on the task of personally shopping for all of Will's Christmas presents for staff and later for his girlfriend, Dani. Her efforts start to go awry when Lydia and Dani's gifts get switched, making Jeb jealous and offending Dani.

Assured by everyone that she's a ""shoo-in,"" Claude applies for the GNB management training program... and Kipp applies too. Meanwhile, Jeb learns that Lydia plans to quit working once they're married, so he enlists Kipp to convince her otherwise; and Owen and Carl conspire to make cash by catching fish in the East River and selling them to the GNB cafeteria, but their plan is endangered when Ramona catches on.

Claude babysits Kipp after his laser-eye-surgery and comes to the realization that he may have paid for the procedure with the company's missing funds that Ramona's been looking for. Meanwhile, Lydia is shocked to learn Jeb is hiding a dirty little secret about the fancy hotel she's chosen for their romantic rendezvous. Owen and Carl help Will train for the upcoming NYC Marathon, but they have a difference of opinion on how Will's diet should be handled.

Claude discovers that Jeb and Lydia are pretending to be romantically interested in her and Kipp, respectively, as a means of making the other jealous. Meanwhile, Carl makes a long overdue visit to a doctor, played by Star Jones Reynolds, who makes him think he has more ailments than he really does