Dennis experiences an identity crisis on Secretary's Day, while Nina tries to lift her spirits.

Maya discovers that organizing a birthday party for Nina is no cause for celebration.

Determined to prove that good-looking people have an unfair advantage in the job market, Maya concocts an experiment. She'll send two people to interview for the same job- one is unattractive but perfect for the job; the second has the brains of a Stegosaurus but is gorgeous. She soon falls victim to the very prejudice she is trying to fight when she and the good-looking guy start dating. Also, Nina begs for the chance to participate in an office prank on Finch while Jack struggles with the complicated assembly instructions to his baby daughter's dollhouse.

Maya's new assistant Cindy is certainly eager, but also incompetent, and Maya's work suffers because of it. Jack wants to fire her, but Maya is determined to give her a chance. However, the more time that passes, the more Cindy screws up, and the more Maya's resolve is tested. Meanwhile, Finch and Elliott sabotage Nina's radio appearance by giving her a phony Word-a-Day calendar.

Maya's attempts to get her coworkers involved in her favorite charity are met with overwhelming indifference. Only after the PR-minded Jack goads them to help to Finch, Elliott, and Nina contribute. And only after Maya pleads with him does Jack finally contribute. Rather than giving his time or effort to the charity, he helps in the usual Jack Gallo fashion- by giving a giant check for $50,000. When he consequently wins an award for Humanitarian of the Year, Maya's jealousy gets the better of her. Meanwhile, Elliott tries to figure out why the office's nickname-happy gopher keeps snubbing him.

A surprise visit from his fireman father leaves Finch puzzled, since the two had always been emotionally distant from one another. When Red Finch suggests that he and his son spend some quality time together, Finch can only surmise that his father is either dying or having an affair. The truth turns out to be even more shocking- Red has finally come to accept the fact that his son is gay. He isn't, of course, but Finch has a hard time convincing him of that. Meanwhile, Maya invites Jack to her apartment to dinner in order to convince him that the neighborhood she lives in is not as bad as he thinks, but a robbery there that afternoon complicates the task.

Finch's complaints about doing petty errands bring an unexpected response from Jack- he hires a personal assistant, Kenny. Having his territory infringed on soon becomes the least of Finch's worries, as Kenny threatens Finch violently when Finch speaks up. To make matters worse, no one believes Finch because Kenny is all brightness and sunshine to everyone else. Meanwhile, Nina's attempts to quit smoking backfire in two ways: Nina becomes even more amorous than usual toward everyone, while Maya, mistaking Nina's nicotine patch for a Band-Aid, gets unwittingly hopped up on nicotine and becomes relentlessly hyper.

While writing his memoirs, Jack suddenly contracts a horrible case of writer's block. He then realizes why- he has come to the place in his memoirs where he fired his old partner Herb just before Blush took off. Discovering that his old partner has been toiling in a toyshop in Connecticut for 30 years earning a meager living only worsens the guilt. In an attempt to make it up to him, Jack gives Herb a high position in the magazine only to rediscover the reason he let Herb go in the first place- Herb is terrible at the magazine business. Meanwhile, Nina's problems with an IRS audit seem to be over when the female auditor takes a liking to Elliott, but in fact, they're just beginning.

Maya senses trouble when Nina proposes a double date for the two of them. She is proved right when her date, after throwing his back out in her apartment, is revealed to be a United States Congressman - and a married one. Afraid of a scandal, he forces Maya to harbor him in her apartment while newspapers overflow with news of his disappearance and rumors of where he might be, and his friends, family, fellow Congressmen, and the police relentlessly search for him. Meanwhile, a friendly game of paintball causes a major office tiff when a fear-crazed Finch shoots Jack a few seconds into battle.

Jack enlists Finch to stop off at his house and check up on his new nanny. However, Finch ends up having sex (""Twice!"") with the nanny. But his joy may turn to embarrassment after he discovers Jack had a hidden camera installed in the room that they used. Meanwhile, Elliott neglects a favor Maya asked him to do, and Nina joins a cult.

Jack wants the tenants on the floor above Blush to move. Maya is taken in by Finch's lie that he wants them to move so he can build a free daycare center. The real reason: a steam room. Meanwhile, Nina meets with her former model roommate, who is now fat.

Not impressed with Maya's lame attempt to play a prank on him, Finch claims that women just aren't as good at practical jokes as men are. To prove him wrong, Maya tries to convince Elliott he's being stalked, but it turns out the joke's on her-in a big way. Meanwhile, Jack fears that he's really beginning to look his age, so he decides to look into plastic surgery.

Finch returns from Jamaica after a failed attempt at romance with Courtney, who played him, as it turns out. Elliott steps in to try to prove what a friend he is to Finch by giving her a dose of her own medicine--getting her hooked on him and then telling her to kiss off. Unfortunately, the plan goes awry when he ends up liking her and they start dating for real. Meanwhile, Jack makes another bet with Donald Trump--whoever loses less weight has to wear a dress during their golf game. However, he makes the mistake of asking Nina for help with his diet.

Jack fears for his reputation when he falls to #100 on the Power 100 list. Nina's idea to improve his standing by sending out a special collection of Blush covers to remind people how important the magazine has been backfires, as Elliott is made #100 because of his brilliant photography. Meanwhile, Finch meets idol Mark Hamill at Bartini's and annoys the hell out of him.

Nina gets into a catfight with modeling rival Margo Langhorne, then becomes upset when Margo decides to retire from modeling. Jack is upset that Donald Trump has a sandwich named after him and gets Finch to attach his name to a park. Maya's new boyfriend enjoys taking his shirt off in public. And Elliott's wearing new shoes to please his girlfriend, but they only make him slip.

With Jack's autobiography out on shelves, a problem is discovered: he claims to have beat up Robert Conrad, only because he thought the actor was dead and couldn't say otherwise. Unfortunately, the actor stops by the office. Finch and Elliott deal with a good saleslady who uses compliments to sell clothes. Nina is upset that she's only mentioned 4 times in Jack's book.

Finch has been sleeping at the office. Elliott's new girlfriend is a cover girl AND student at Yale medical school. Nina starts sleeping at the office too after Binnie kicks her out. Maya is jealous of Kaylene but after she accidentally causes Kaylene to break up with Elliott, she must find a way to get them back together. Finch and Nina have fun together but he feels betrayed when Binnie invites her back.