Finch realizes that he and Adrienne are very different from one another and begins to doubt their marriage. Meanwhile, Jack asks Maya to do the annual employee evaluations.

Jack and Maya run into his ex-wife Roberta on an airplane to Paris. Jack desperately tries to convince her to marry her new boyfriend so he can stop making alimony payments. Finch and Elliott convince Nina that Jack is still in the office, until she discovers their prank and enlists Kevin the mail guy to help get them back.

Elliott doesn't want to tell the office about his new relationship with Maya, while she is quite anxious to. They try to keep it quiet, but everybody quickly finds out.

Finch, desperately seeking an apartment, convinces Maya to move in with Elliott. But when the two fight on their first night together, Finch may be in trouble when Maya returns home and he has a woman in his bathtub. Meanwhile, Jack and Nina argue on the anniversary of their first meeting.

Finch goes undercover at a high school and winds up becoming incredibly popular, and having the head cheerleader ask him to the prom. Jack discovers that the office mail guy is an incredible opera singer. Nina becomes celibate, following some advice from Elliott. Nina and Finch kiss.

Nina and Finch don't know about Jack's divorce yet. Jack moves into the Plaza Hotel for privacy. Maya wants Elliott to read an article about relationships but he doesn't, which causes problems. Everybody gathers in Jack's room. Finch and his singing group, 2 Fine, perform.

Elliott's brother Donnie returns as a successful insurance salesman in need of a loan. Maya, however, remains convinced that Donnie is up to his old tricks, even when he is beaten up. Jack and the rest of the staff discover that silence is not always a good thing.

Maya is reunited with her best friend in high school, Alan, who is now a successful motivational speaker. However, Alan confesses to Maya that he is a recovering alcoholic, but another revelation causes the trouble: he was responsible for her school shunning her. When Maya is unable to forgive him for this, he begins drinking again, disrupting the motivational talk he is to give at the Blush office. Meanwhile, Jack is frightened because of a recurring dream he has about Kevin.