Allie returns and asks Jack for a job at Blush, but she has ulterior motives. Nina meets with Elliot's new girlfriend, who is a psychiatrist, but their session means trouble for Elliot.

Maya picks up a guy in a bar and finds he's not quite who he claims to be. After being the recipient of an act of kindness, Elliot tries to convince Finch to pay it forward to Nina.

Finch becomes the boy toy of a popular romance novelist. Nina says the wrong thing on the red carpet of an award show.

Finch's mom comes to visit and finds romance. Elliot meets a famous photographer who is down on his luck.

Nina's younger sister come to visit, bringing up feelings of jealousy in Nina when the staff falls in love with her.

After his close friend dies, Jack worries that an old secret might impact him and Maya.

Finch DJs a bar mitzvah for a kid who has a crush on Nina. Jack and Elliot like the same woman.

Finch and Maya project their insecurities on the new intern, Dean. Nina is dating the famous magician, Zigmund, who everyone is convinced is gay and Elliot believes is flirting with him.

When Elliot discovers that Maya has a date for the Blush Charity Auction, he asks Nina to set him up with someone to help make her jealous. So Nina sets him up with a doctor but when she can't make it, she hires an escort instead. 

Elliot's commitment phobia causes him to have a massive panic attack when Maya accepts his marriage proposal. Meanwhile, Nina helps Finch sell his adult movie script.

When Jack's ex wife returns her engagement ring (a Gallo family heirloom), Elliot is inspired to propose to Maya.Finch goes to great lengths to assist Elliot in making everything perfect but the cancellation of Nina Van Horn day throws a spanner in the works.

When the new girl in marketing asks Nina and Maya to her bridal shower, they are convinced the only reason is so that she gets more gifts. Nina confronts Robin, and Nina and Maya end up arguing. Meanwhile Elliot has to go to traffic school and Finch is the teacher.

Finch dates a female boxer with a jealous ex-girlfriend. Elliott, Jack and Nina fool Maya into believing that they're smarter than she is.

Jack's numbers come up in the lottery, but Finch spent the money on coffee instead of the lottery ticket. Meanwhile Maya and Elliot get a dog, but Finch and Nina convince Elliot that Maya is using the dog as a substitute for a baby.

Finch gets tired of Jack's constant demands and loses his cool. He apologises later but Jack asks him to help in the data entry department. Upon arrival, Finch finds Jack's former assistant.

Maya attempts to hold a Thanksgiving feast for the gang but Jack sleeps with Elliot's mother. 

When Finch reunites with his childhood friend, he is shocked to learn that he had a sex change and is now a woman named Brandi. Finch finds himself attracted to her.

Maya's best friend from high school, now a successful motivational speaker, is hired to speak at Blush. As part of his recovery from alcoholism, he confesses he started a rumour about Maya back in high school.

Elliot's brother Donnie (who once feigned being mentally challenged so that he could be waited on by his mother) returns. He claims to have found a job, but Maya is skeptical. When he is supposedly beaten up and winds up in a hospital, she thinks it's a con and attacks Donnie.

When Nina begins dating an actor she has to compete with his mother for his attention. 

Tired of everyone's pity after the news of his impending divorce, Jack heads off to the Plaza Hotel. When Finch turns up with his new band, Jack loses his cool.

After their moment of passion, Finch decides it's a bad idea to take things further with Nina. NIna becomes determined to find out why. Meanwhile, Elliot overhears, and then accidentally erases a message from Ally telling Jack she is leaving him.