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- Three different, but related, families face trials and tribulations in their own uniquely comedic ways.
- Meet the people flying between LA and Vegas on weekends.
- A neurotic book editor is paired with an eccentric writer.
- The hilarious misadventures of an 11-year-old boy and his wacky family in 1962.
- Maya goes on a date with the office exterminator, Chris. She will be amazed at how much she actually likes him, though he is not the smartest. Finch and Elliot amuses himself by paying Kevin to eat junk.
- As Dennis tries to hide his true passions from his new supermodel wife, Maya and Elliott seek to have their accidental marriage annulled.
- Jack checks into Plaza and he can't find any peace and quiet after Maya and Elliot have an argument, Nina comes uninvited and Finch makes a live performance of his boy band.
- Simon is prepared to ask Nina to marry him - - turns out she been married for 8 years and is powerless to ask for a divorce. Jack finds the perfect guy for Maya but she falls for someone else.
- Maya's old boyfriend, an actor who went to England to join a Dramatic Academy comes back to town and reconnects with her. And Jack is not happy to see cause he didn't like him and walked in on them in flagrante delicto. It's when Jack is expressing his disapproval of him that he blurts out how the guy got into the Academy.
- A&E Biography looks at the troubled history behind the career of Nina Van Horn.
- Jack sets up Elliot with a fake headhunter to test his loyalty. Elliot proves he's loyal but resents the set up. He teaches Jack to swim so he'll become more trusting. Finch creates a fake kid so he can trick a nanny into sleeping with him.
- Jack sends Maya to an N.Y.U. seminar as a guest speaker for the magazine, but she gets ambushed, instead. She finds it hard to refute their claims of Blush's objectification of women. Nina's gold, but she can't wash off Elliot's paint.
- Maya becomes a pawn in the ongoing competition between Elliott and his old college classmate.
- Maya, Nina and Elliott are all nominated for a prestigious fashion magazine award.
- Nina pesters Eliot to set up a therapy session with his new girlfriend. Alie wants Jack back.
- A writer in need of a job reluctantly agrees to work for her father's women's magazine.
- An imposter claims to be Jack's son.
- A photographer coerces Elliot into hiring him as his assistant. Elliot doesn't want to be under his thumb but doesn't know what to do. An astronaut comes to for an interview but Nina thinks the whole going into space is a hoax.
- Maya dates an obnoxious blind man who thinks his disability makes it okay to be rude. Finch takes a class in T.V. broadcasting and helps produce a show where he surprises his guests by attacking them.
- When the conservative Citizens for Morality demands that the magazine tone down their sexually explicit covers, Jack is sure that his charm can easily diffuse the situation.
- The Blush staff agrees to corporate therapy after their bickering drives off a client. Dr. Drake complicates their teamwork when he advances Finch and Nina to blue binders, while Maya and Elliot sill have their red ones.
- Finch meets up with an old friend and is ashamed of his feelings; whilst Elliot gets back at Nina for treating her assistant badly.
- Finch is threatened by Jack's new assistant.
- When Nina's long-time friend passes away, she finds it hard to cope with the loss. At first, she avoids the whole issue. Later, she can't separate herself from Binnie's ashes and takes the urn with her everywhere. Dennis feels threatened by Jack's new egg-shaped electronic personal assistant, but finds relief when Jack agrees to pay to send Dennis to college.
- Maya's high school friend tells her he is responsible for a bad rumor that caused her unpopularity. He's come back to make it up to her. Jack dreams about Kevin killing him. His nightmares continue until he confronts Kevin in an elevator.
- Jack's daughter, Hannah, makes an appearance. Jack must set things straight with a little boy she creates a scene with, waiting to see Santa. Maya meets a handsome celebrity who loves Christmas even more than her, to the point of obsession.
- When the student she's been mentoring for several years comes to visit, Maya takes care to warn her dad and the staff to be on their best behavior. Despite getting good grades and having lots of friends at school, Karey senses that something still isn't quite right with her life. Recalling how she once turned down an opportunity to study in Paris during her own college years, Maya encourages Karey to pursue something she's passionate about. Meanwhile, Finch agrees to fill in for Jack's wife at the Gallo's regular bridge game. After encouraging Karey, Maya is stunned to find she's decided to become a model. And while Maya tries to point out the many pitfalls of getting a modeling career off the ground, Elliott reveals that she already has a number of offers to work. However, Nina begins to have second thoughts about pushing Karey to model after discovering she's also a gifted poet.
- Eliot tries to date Vicki but ends up with her sister. Jack monitors the office remotely with a 2-way A/V system.
- Nina's former agent whom she cast aside when she made it big calls her and she makes an unusual request. When Nina has to do something she passes her to Finch who hits it off with her. Maya thinks her new boyfriend has unusual fetish.
- Maya and Elliot take in a lost dog. Everything is fine until Finch convinces Elliot that Maya has gotten the dog to test his fatherhood skills. Meanwhile Jack wins the lottery but Finch never bought the ticket in the first place.
- Good-hearted Elliott discusses business strategies with his con artist brother Donnie. Nina enters a fierce game of chance with Jack.
- 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 is in trouble with some loan sharks but Maya is completely skeptical. When he is supposedly beaten up and winds up in a hospital, she thinks it's a con because all of the hospital staff were at the bistro where she and Elliot met Donnie, thinking they were there to make it appear that they were in bistro. So Maya attacks Donnie.
- Jack agrees to pay for tutoring because Finch isn't doing well in college. After learning his tutor is also a masseuse, Finch trades the tutoring sessions for massages. Elliot shows a nude photo of a sleeping Maya at an exhibition.
- Elliott is made to realize that he was a nerd in high-school. Now he feels even more unsure about himself 20 years later.
- Everyone likes Nina's younger sister Erlene, who comes to New York for a visit. Nina is jealous and plots to give her the boot.
- Jack asks the staff to evaluate his work anonymously. Nina ends up with a sprained ankle after a walk.
- When Jack's ex-wife Eve drops in unannounced, her long-standing hostilities with him are renewed. Tired of always having her parents fighting, Maya threatens to stop talking to either of them if they can't behave. And hoping it will make things better, she suggests that her mom and dad join her for dinner. Meanwhile, on Jack's invitation, Bill Slatton arrives at the office determined to make the staff work harder. After agreeing to the dinner date, Jack begins to suspect that Eve has come to take back a favorite painting he's supposed to give up as part of their twenty-five year-old divorce settlement. And once Maya lets it slip over dinner that Jack is worried, Eve seizes upon the idea of getting the painting back. Meanwhile, Nina and Finch both find it hard to outwit Bill's efforts. And even though Elliott tries to meet the new standards, Bill sees through his efforts to brown-nose.
- When Finch's newly single mom shows up, he tries to fix her up with Jack so that he can be part of Jack's family. He sabotages Jack's current relationship for the plan to take effect. Elliot learns that a once great photographer has been slumming at Nina's, he's now a 'down and out'. So Elliot tries to help him.
- Maya has a problem when a reporter scheduled to pose as a high school student calls in sick. Needing someone for the assignment, Jack turns to Finch.
- Jack's new point system causes Nina and Maya to compete for his approval. Finch and Elliot compete over Amy, each trying to outdo or embarrass the other.
- Finch is forced to protect Adrienne from a suitor who is a lot like him.
- 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.
- When Jack catches Dennis with his wife, he throws him out. Later Dennis gets a job working for Snoop Dog. When Jack learns of what happened between Dennis and his wife he tries to get Dennis to come back but he's afraid to tell Snoop that he wants to go.
- The unexpected arrival of his old figure skating partner has Finch worried. Following an accident on the ice nearly twenty years ago that ended her skating career, Nicole stopped speaking to Finch. And while he was upset over losing a partner, the hurt.
- Maya and Elliot are going out on a date. But Cindy, Maya's former secretary who's now a media buyer wants to get space in the magazine. So she goes out with Maya and Elliot and they all get drunk. Elliot wakes up to find himself in bed with Cindy. When Maya learns of this, she's shocked and wants nothing to do with Elliot. Finch trying to get over the end of his marriage to a model thinks he should hook up with another. While Jack tries to get him to take up a hobby.
- Nina feels threatened by Skyler, an old fling of Simon. Skyler would be the minister at their wedding reception. Jack and Finch scam to get rid of her. Meanwhile Maya has found the perfect man, who turns out to be a senior in High School.
- Kevin and Finch become roommates, and neighbors with Maya. She's not happy Finch still has a key to her apartment. Elliot sells Jack his beloved sports car, but isn't happy when Jack shows less love towards the car.
- Finch challenges Maya to play a good practical joke.
- Jack suddenly announces his retirement and puts Maya in charge. He tries to escape an office farewell party in his honor.
- Jack hires a woman off the street to run the desk, but the staff thinks it's just because Jack wants to seduce her.