Maya does an experiment to prove that good-looking people have an unfair advantage in the job market. Also, Nina wants to participate in an office prank.
Maya gets a new assistant who is very eager, but proves to be very incompetent.
Jack is upset to learn that Maya's new boyfriend is the same age as him. Also, Nina causes the window washer to fall from his perch when their flirtation gets out of hand.
Finch dates Elliot's ex-girlfriend Nikki, a model and total nutcase.
When Jack's two tickets for a play in London become available, the Blush gang competes for the trip.
After Maya writes a fantasy story about a dinner with Woody Allen, she is pursued by a Woody Allen impersonator. Also, Jack temporarily loses his eyesight.
Jack tries to get his daughter, Hannah, into a prestigious school, but Maya's past at the school mars his attempts. Also, Nina and Elliott bond over music.
Maya tries to get the gang to contribute to charity.
Instead of exchanging gifts, the staff donates gift money to a janitor.
Elliott's deals with his past as a nerd after his favorite high school teacher dies.
Trying to compete with an old friend, Maya winds up spending a night in a sewer. Also, Nina and Finch get Jack's boyhood idols - Cowboy Pete and his orangutan - as a surprise for his birthday.
Maya is sued for sexual harassment.
Finch learns that his fireman father has always believed that Finch was gay.
When Jack becomes uncharacteristically grumpy, the staff try to figure out the reason for his changed demeanor.
When Maya lands an interview with a legendary rock star, Nina recalls an affair she had with him. Also, Elliott is jealous of Annie Liebowitz and Finch tries to get rid of an ugly vase.
Maya tries to persuade a college student to stay in school but Nina wants the girl to pursue modeling. Also, Finch becomes bridge partners with Jack.
Nina donates her bikini to the Model Cafe, but when they display it over a dumpster, Finch and Maya conspire to steal it back. Also, Jack poses for boudoir photos.
Elliott asks Maya to pose as his wife so that he can get a great deal on an apartment, but when they're forced to kiss, they realize that they have an attraction for each other.
Finch feels threatened when Jack hires a personal assistant. Also, Nina tries to quit smoking.
Feeling guilty over firing his old partner at Blush, Jack hires him back as managing editor. Also, a female IRS agent who is auditing Nina takes a liking to Elliott.
Maya goes to an forum in Jack's place and is ambushed because of Blush's portrayal of women. Also, Nina poses in gold body paint in an attempt at making a comeback.
After Maya insults a famous designer, she has to make amends. Also, Jack helps Elliott with his new girlfriend.
At an office blood drive, Finch, Elliott, and Nina recall how they were hired by Jack.
When Maya's mother visits the magazine, she fights with Jack over a painting. Also, an efficiency expert is brought in by Jack.
Maya's date, as set up by Nina, turns out to be a married politician. Finch loses his cool during an office game of paintball.