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.

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.

Elliott goes to traffic school where Finch is his teacher. Nina and Maya debate why they were invited to a coworker's bridal shower. Jack accidentally sets Kevin's pet tarantula loose in the office.

Jack doesn't like Finch's gift of dog tags. Nina hooks Elliott up with a ""friend"" for Jack's charity auction after he discovers that Maya has a date already. The ""doctor"" turns out to be an illiterate hooker. Finch, acting as auctioneer, tries to undermine the auction when he discovers that Jack threw his gift away.

Jack's ex-wife Allie demands a job at Blush as part of their divorce settlement. However, she reveals to Finch that it's merely a plan to win Jack back. Plans backfire when Finch sleeps with Allie as Jack prepares to walk in on them. Meanwhile, Nina ruins Elliott's relationship with a therapist.

Jack discovers Finch and Allie; he fires Finch the next morning. Two weeks later, Jack has a new secretary, for whom Elliott and Nina cannot decide their feelings for. Finch wants to come back, but finds a job as Snoop Dogg's assistant when Jack refuses. After Allie tells Jack the truth about how she came onto Finch, he decides that he wants his old assistant back.

Maya is looking for a new assistant and thinks she's found the perfect one when Amy Watson, a good looking, young and intelligent woman shows up at the office. The entire male staff of Blush is drooling over her, and Nina warns Maya about Amy, but she thinks Amy is not just another dumb blond bimbo. Amy tries to show Maya some articles she has written, hoping that they would end up published in the magazine, but Maya thinks their content doesn't go with the Blush's theme. Nevertheless, Amy goes over Maya's head and shows the articles to Jack, who makes her Blush's newest sex columnist. Maya, who was just convinced to fire her because Amy was not at all what she thought, is shocked. Meanwhile, Elliot finds himself in an awkward position after setting Kevin up with a woman.

Finch and Elliot are fighting over Amy. Jack warns Amy that the fight is interfering with the office work environment, and so Finch and Elliot come to terms about Amy: they decide that since they both like her so much, they should share her, meaning she would spend half her time with one and then the other half with the other. Of course Amy is not ok with that and decides to quit the magazine altogether since she got a six figure book deal. Meanwhile, Jack and Nina try hard to show Kevin the good of being rich and end up corrupting him. Now Kevin, who was once happy and simple, is miserable and full of debts.

Nina is tired of Kevin's obsession with her and his sick, weird gifts, so she asks Maya to tell him to back off. Maya agrees, but assures Nina that Kevin is just a sweet guy and not the weirdo she thinks he is. Later that night, Maya is surprised at her building by Kevin and gets a little freaked out. Her suspicions come true the next morning when Kevin tries to return a quarter she dropped while entering the lobby. Maya yells at Kevin, who runs away shocked to discover everyone thinks he's a pervert. Maya sends Nina to talk to him, and Kevin confesses his feelings for her and asks for a kiss, which she reluctantly agrees. Surprisingly, he kisses her forehead. Meanwhile, Jack has to suck up on an arrogant millionaire so he can launch a Blush channel on cable, and tries to bribe Elliot so he can be laughed at and made fun of by the millionaire. But Jack is forced to interfere when the guy crosses a line with his friend.

It's Christmas time and Jack throws his annual party at the office. He dresses up as Santa, and tells Elliot's nephew that he won't get any presents for being a naughty boy and pushing Hannah out of the line. When Jack finds out the truth that Hannah made it up because she thinks she can do anything and her daddy owns the world, he has to apologize to little Paul, but only make things worse. Meanwhile, Kevin's cousin Ray Liotta attends the party and sparks fly between him and Maya. But Ray's odd obsession with Christmas scares her away. And Finch and Nina fight over who creates the best new Christmas song. They can't come up with anything so they decide to become Jewish.

Ray Liotta appears on ""The Tonight Show,"" pledging his love to Maya. She rejects him until he agrees to give up being in the public eye for her, although he finds it difficult to adjust to being a regular guy. Elliott and Finch play a joke on cocky Jack, who has bought a desk once owned by George Washington. And Nina creates a one-woman show based on her life.

Finch schemes to hire a sexy au pair to care for his nonexistent son. Elliott and Jack have trust issues after Jack gives Elliott a loyalty test.

Maya's noisy neighbor moving out clears the way for Finch and Kevin to move in. But when Finch is given a space in the dorms on campus, he may leave Kevin out in the cold. Meanwhile, Elliott has trouble parting with his vintage car when he sells it to Jack.

Nina talks Maya into dating a handsome but dumb exterminator. Maya is tested when she meets a smart man at an art gallery and sleeps with him. Meanwhile, Jack tries to teach Elliott and Finch a lesson when they begin paying Kevin to eat weird things.

Trying to find a photo for a show, Elliott chooses a nude photo of Maya he took when they were dating and she passed out drunk. Jack hires a tutor for Finch, although she turns out to be a massage therapist as well. When Finch confesses he got a massage instead of being tutored, Jack is happy because Finch is maturing.

In a satire of ""Project Greenlight,"" Finch makes a ten-minute semi-autobiographical movie for his film class, and convinces actor David Hasselhoff to play the father in the film. But when filming starts, trouble ensues when Nina, playing the mother, falls in love with the actor playing her son. Meanwhile, Jack demands an onscreen apology from Hasselhoff after the actor scratches Jack's car in the parking lot.

Elliott becomes distraught when his grandmother becomes more interested in spending time with Finch than her own grandson. Meanwhile, Maya wants to bring a little patriotism to the Blush office with small American flags for everyone, but Jack decides to make a grander gesture, with disastrous results.

Nina is dating the lead guitar player of Finch and Kevin's new ""air band"" and convinces him to quit the group. Meanwhile, Jack's rivalry with Alan Thicke drives both of them to therapy with their daughters.

Maya's tryst feeds office gossip, thanks to blabby Nina; Finch's scheme for a reserved parking space runs afoul of prying Elliott.

The series finale centers on a send-off for retiring Jack, whose staffers share memories, shed tears and pay affectionate tribute. Finch puts his feelings into rap, while Nina likens Jack to---what else?---"a perfect glass of Scotch."

Vicki's back in the hairstyling biz and is now dyeing to give Blush the brush; Nina takes under her wing a female impersonator who's going to portray her in a cabaret show; and Dennis rides roughshod over Elliott, his new assistant.

A boycott of Blush is threatened by a feminist, whom Jack uncharacteristically finds "very interesting [and] attractive". Also: a male-bonding feud pits Finch vs. Elliott; and dreams of infidelity haunt Nina.