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.

Finch reveals his personality is not his own but one he ripped off a girl he knew earlier in life. Jack asserts his alpha-male status when Elliot refuses to share his cannolis.

Finch dates the woman who shares his personality. Nina doubts her ability to negotiate a raise from Jack, and Maya wonders if her raises are just because she's his daughter.

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 new assistant will stop at nothing to get ahead fast. She goes over Maya's head to get Jack to hire her as the new sex columnist. Elliot sets Kevin up with a date, but Kevin can't let Elliot go.

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.

The competition between Finch and Elliot kicks into high gear when Amy asks them each out for a date on the same weekend. Jack and Nina entice Kevin with the finer things after he turns down a promotion because he doesn't care about money.

Kevin begins stalking Maya instead of Nina. Jack must tolerate his snobbish business partner's attempts to degrade those less fortunate, namely Elliot.

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.

Nina reveals she had a child when she was younger. And that child who is now a woman has come looking for her. Nina not wanting her to think less of her asks Finch to pretend to be her son.

It skips a generation. Nina's newly discovered granddaughter shares much in common with her, in fact, too much. Nina wants her to show some restraint. Jack tries to find the perfect gift for Maya's birthday, only it's not her birthday.

Ray Liotta is back and he's obsessed with Maya. He even vows to give up show business for her, but can't adjust to normal life. Jay Leno also appears as himself. Nina puts on a one-woman show. Jack buys George Washington's desk.

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.

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.

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.

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.

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.

Jack wants to write a novel but ends up using a ghostwriter. With him out of the office, Nina, Elliot, and Maya compete for power over the magazine. No one produces much of anything related to quality.

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 produces a low-budget movie with the help of his coworkers and David Hasselhoff. Things go wrong, like a flaming bird house tragedy, Jack's scratched car, and Nina's physical affections towards her "son."

Elliot's grandmother offends him when she lavishes attention on Finch but ignores Elliot. Jack hangs a giant American flag on the side of the building. Nina thinks it makes the building look fat, and it turns Jack's office blue.

Finch's fellow band member, Greg(Huey Lewis), asks Nina out. She's mortified when she finds out they have an air band with imaginary instruments. Alan Thicke brings out Jack's competitive side. Maya gets upset when Jack drags her into it.