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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.
- The hilarious misadventures of an 11-year-old boy and his wacky family in 1962.
- A neurotic book editor is paired with an eccentric writer.
- 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, but she's been married for 8 years to flaky Roland Devereaux and asks Elliott for moral support in asking for a divorce. Jack finds a 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.