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.

Jack and Finch discover a pneumonic-message system in the wall. Meanwhile, Elliott invites Maya to his house for his ""slow"" brother's birthday party. At the party, Donnie reveals to Maya that he's not really ""slow."" Maya tries to tell Elliott that Donnie's not stupid, but just ends up looking silly herself. Jack's inanity causes Donnie to reveal his act. And a gift of a parakeet explodes into a living nightmare for Nina.

Magazine owner Jack Gallo makes peace with his estranged daughter when she asks him for monetary help--and lands a job at the mag.

Jack returns from China with exotic and mysterious candy that has strange effects on the staff.

At first, Elliott's attempts to warn Finch about dating his ex-girlfriend, supermodel Nikki Elston, seem like just jealousy. However, there's more than a grain of truth in his warnings- Nikki is a true nutcase who delights in putting men through hell. One of her favorite stunts is locking them on a perch in a giant birdcage. Meanwhile, Nina's attempts to get a raise from Jack are subverted by the discovery of the truth about her use of the company's expense accounts.

An ordinary office blood drive turns into a storytelling session, as Finch, Elliott, and Nina relate to queasy donor Maya and nurse Tisha the tales of how Jack rescued them from rather desperate situations. Finch applied his shiftiness to a job as movie usher before the manager fired him for trying to sneak a customer into a sold-out show. Luckily, the customer, Jack Gallo, took notice of his methods. Elliott was a down-and-out amateur photographer reduced to selling his output on the street and faced with the prospect of taking a job at a grocery store in New Jersey, but in the nick of time, his talent was noticed by a patron named Jack Gallo. Finally, Nina had come a long way from her successful modeling career--she wore a mermaid suit at a boat show before someone stopped by who remembered her keen fashion sense--none other than Jack Gallo.

On her first day at work, Maya decides to do a hard-hitting story on child labor overseas, while Jack tries to distract her with a plush office.

Maya's life becomes a nightmare when her co-workers discover that she's had a sex dream involving Elliott.

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.

Jack has a slight problem with Maya's new boyfriend- he's the same age as Jack. When he voices his disapproval to Maya, she accuses him of being hypocritical, since he married someone her age. Both parties are left with a personal dilemma. Jack wonders if he is in fact being hypocritical, and Maya wonders if she may be dating the man to get back at Jack. Meanwhile, Nina's flirtation with a window washer proves hazardous to his health.

Jack has two tickets to a London performance of King Lear, but when he is forced to cancel his plans, he is forced to decide who to give the tickets to- the suck-ups Nina and Elliott, who just want the vacation on his private jet, or true Shakespeare die-hard Maya. The adventure that follows parallels the play. Nina and Elliott get the tickets, but their endless conniving against each other proves to be their undoing, while only Maya stays true to her father.

Maya's fantasy piece about a dinner with Woody Allen brings notice from a lot of people--including Woody Allen himself, supposedly. The man who shows up at Maya's office the next day is not Woody Allen, but he presents himself as such, and actually seems to believe he is. Maya finds herself playing along with the charade until their relationship and her life turn into her favorite movie, Annie Hall. Meanwhile, a mix-up over eyedrops causes Jack to temporarily lose his sight.

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.

At Maya's urging, the gang agrees to forego the usual gift-giving tradition and pool their money into a donation for someone less fortunate than they are. The recipient turns out to be night custodian Jesus Santos, whom Maya meets while working late one night. Things become extremely awkward when Jesus decides what to spend the money on- nothing but presents for Maya. Meanwhile, Finch conspires to get Elliott to let him tag along on his trip to the Caribbean for a Christmas photo shoot with five gorgeous models.

The arrival of Maya's old college roommate Erin leads to an incredibly crazy situation. Maya tries to compete with her friend's globe trotting journalistic ventures by spending a night in a sewer in hope of getting her first hard-hitting news story in a year. In the meantime, Erin takes a break from her hectic schedule and has an affair with Elliott. Adding to the craziness is Jack's surprise birthday party, with Nina and Finch supplying his boyhood idols, crazy old Cowboy Pete and his orangutan sidekick. In the end, though, it's Maya who provides the biggest surprise of all.

When Maya scores an interview with legendary rocker Nick Hewitt, a flood of memories is triggered for Nina of the affair they had 25 years ago. Nina describes it as the most romantic weekend of her life, and she realized he felt the same way when the song ""Nina in the Cantina"" hit the charts a few months later. Unfortunately, Maya learns that the song was actually about Twiggy, and Hewitt only used the name Nina for the purpose of the rhyme. Worse, he doesn't remember Nina at all, leaving Maya to engineer a big charade to keep Nina from getting hurt. Meanwhile, Elliott's extreme jealousy of Annie Liebowitz is exploited everywhere he turns, while Finch tries desperately to get rid of an ugly handmade vase given to him by Jack.

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's mother visits the magazine and promptly becomes embroiled in a battle for a painting with Jack. Meanwhile, a new efficiency expert ""hired"" by Jack turns out to merely be Jack's golf caddy.

Nina worries when her biological parents come to visit. A blood test proves that she is not their daughter but she lies and tells them that she is, until Maya discovers that the two are merely con artists. Meanwhile, Elliott and Jack become jealous when they discover that Finch is extremely well-endowed.

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.

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.

Jack desperately wants to get his daughter Hannah a spot in the prestigious Woodbridge School, but there's one slight problem. The Gallo name isn't exactly a hallowed one there since former student Maya once burned down a wing of it. When the headmaster blames Jack's failure to take an interest in Maya's life for the incident, he has his hands full trying to right two wrongs - one to the school and one to Maya. Meanwhile, Elliott and Nina bond when they discover both are fans of blues musician Cholera Joe Hopper.

When his favorite high school teacher dies, Elliott at first sees the memorial service as an opportunity to flaunt his flashy career and his glamorous lifestyle in his old classmates' faces. His cockiness is quickly tempered, however, by the revelation of the truth about his high school years- he was something of a nerd. When the office hears about it, his present becomes almost as intolerable as his past. Meanwhile, Jack trains Finch in the art of being influential around the office.

When Maya develops a crush on a writer she works with, she isn't quite sure how to handle the situation. Believing he likes her, but is too shy to ask her out, Maya takes some tips from Nina on how to lead him on. The strategy backfires when Maya finds herself slapped with a sexual harassment suit the next day. Meanwhile, Elliott tries to live down his humiliation when he discovers his girlfriend is a spokesperson for a brand of hemorrhoid cream.