Jack challenges Elliott to a game of darts and hits him in the back when Elliott accuses him of being too competitive. Meanwhile, Nina reveals that she had a daughter 34 years ago that she gave up for adoption, and her daughter is trying to find her. Nina enlists Finch to pose as her ""son"" but when she tells her daughter the truth, she wants nothing to do with her. Trying to make amends, Nina discovers that she is a grandmother also.

Nina is trying so spend some quality time with her granddaughter Tess. Chloe asks Nina to keep Tess from bars, boys and clubs, but all Tess wants is to get wild. She throws herself at men at a bar and later at Finch, who pretends to be the magazine's editor. When Tess runs away, Chloe and Nina find her at Dennis's, and they all offer to sleep with him in order to keep Tess from doing so. Meanwhile, Jack insists on giving Maya a birthday present, but has no luck with his ideas or Elliot's. She gets mad not because of the meaningless gifts, but because it's really not her birthday and her father should know better. Still, they both feel like it's someone's birthday – and it is: Maya's mother!

Nina's long time friend Binnie unexpectedly dies, and Nina has a hard time dealing with it until Elliot confronts her. From ignoring her death, Nina takes a weird turn to worshiping and hanging out with her urn, until she loses her friend's ashes. Meanwhile, Jack has a new pet: a mini-computerized egg that will do almost everything Finch does, causing him a great deal of jealousy. Finch then decides it's time for him to do something that will take him to the higher steps of life and go to college – through the Gallo Foundation Scholarship, that is. Unfortunately, Maya is there to bring the good sense down to her father, and he ends up giving the scholarship to someone who really deserved it: the eastern European cleaning lady's grandson.

Jack hires Betsy Frayne as the new security officer for the office, and Finch freaks out. Betsy went to college with him, and Dennis says she stole his personality. The Blush staff has Betsy thrown out of the building and fired, and are about to call the police when Dennis admits that he was the one who stole her personality back in college. Betsy is rehired, and now Dennis has to find another personality or settle with his dull (but true) personality, Denny, while Betsy confesses her true intentions of seducing Dennis. Meanwhile, Elliot forbids Jack from eating his cannolis after Maya and Nina accuse him of being Jack's bitch and Jack decides to get back at Elliot using his social influences, until Elliot can't take it anymore and gives Jack his last cannoli.

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.

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.

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.

Elliot encourages Dennis to give Betsy a chance, since he thinks she's perfect for him. Although reluctant at first, Finch finally gives in and discovers the wonders of being in a healthy relationship. That is, until Betsy makes an inadvertent move on Elliot and proposes a threesome, which freaks Finch (and Elliot) out. Meanwhile, Maya struggles with the possibility of her father giving her special treatment when she asked for a raise and pretends she is leaving the magazine.

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 Elliott compete for Amy's affections, with Finch finally gaining the lead after an emergency with her beloved cat. Meanwhile, after Jack introduces a point system for positive reinforcement, Maya and Nina only use it as a source for competition.

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.

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.

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.

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 dumps a blind man named Jay, whom Maya feels sympathetic for. Jay asks Maya out for a date at the movies, which she thinks at first to be a nice and interesting experience. But her opinion quickly changes when she discovers that Jay tends to lash out his anger publicly. She tries to dump him, but he convinces her that he'll behave. He comes over to her place to watch some more movies, but Jay brings porn and Maya kicks him out for good. Meanwhile, Jack encourages Finch to take some useful classes in college, so Dennis takes on TV Production. He starts his own show - "Finch Attack!" - and asks Elliot to be his first guest. Halfway through the interview, he literally attacks Elliot and tapes him to the chair. After apologizing, Dennis convinces Elliot to help him attack Jack, but instead they both attack Elliot again.

Jack takes a vacation and uses the time to fulfill his dream of writing a novel. But when he gets frustrated, he pays an English professor to write the book for him. Meanwhile, Maya, Elliott and Nina are left to oversee the magazine and can't agree on even the smallest decisions.

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.

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.

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.

After the staff embarasses themselves in front of designer Kate Spade, Jack hires a corporate therapist.

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.