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 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.

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.

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.

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.

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.

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.

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 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.

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.

What starts out as a normal, everyday office meeting turns into a huge enigma when the easygoing Jack suddenly loses his temper for no apparent reason and refuses to talk about it. The gang takes it upon themselves to discover the reason for his outburst, but with every lead they follow, the mystery just gets deeper and deeper. While this is going on, Finch tries to attract a pretty coworker by following Elliott's advice and playing hard to get.

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.

Mentoring seems to be going really well for Maya- her protege; Karey is doing fabulously in her first year of college. However, Karey is now at a crossroads wondering what to do with her life. Maya tries to push her to stay in school and make the most of her college years, but she hits an obstacle in the form of Nina, who wants Karey to put her natural talents to use as a model. Meanwhile, Jack and Finch have an illicit "fling" with each other—as bridge partners.

It's a day to celebrate for Nina: her famous bikini is about to be put on display in the Model Cafe, a sort of Hard Rock Cafe for supermodels. Her mood turns from celebration to despair, however, when she finds out exactly where in the cafe it is being displayed—over a dumpster. Finch and Maya, concerned over their friend's feelings, conspire to steal it back for her. Meanwhile, Jack has Elliott take boudoir photos of him as an anniversary present for his wife, but neither model nor photographer is without reservations.

It all starts out innocently. In order to help Elliott get a great deal on an apartment, Maya agrees to pose with him as a married couple. To complete the charade, the two are forced to kiss. This development is harmless enough… until they find themselves kissing again voluntarily. "Awkward" could hardly begin to describe relations between them afterward. They work through it, but by the end both Maya and Elliott realize that the long, bumpy road, wherever it may lead, is just beginning for them. Meanwhile, when Jack discovers Finch has been renting out his parking space, it leads the two into a battle over trust.

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.

When Jack sends Maya in his place to an NYU forum on Women in the Media, she sees it as an opportunity to speak up for the viewpoints that Blush often tends to push by the wayside. Unfortunately, she never gets the chance, as the forum turns out to be an ambush, where Maya is crucified for Blush's negative portrayal of women. She ends up lashing out at everyone at Blush, but things only become worse when her comments find their way into NYU's campus newspaper, which Finch promptly distributes at the office. Soon afterward, the truth is discovered- Jack knew all along what would happen at the forum, and it's left up to Maya to turn the tables. Meanwhile, Nina attempts to stage a comeback by posing in head-to-toe gold body paint for Elliott, but her constant sniping at the photo shoot annoys Elliott so much that he pretends to be out of the solvent required to remove the paint, leaving Nina to walk around golden for a few days.

Maya and Finch attend designer Oscar Milos's fashion show using Nina's tickets. At the party, a drunken Maya makes some caustic remarks to a newspaper reporter, resulting in Milos pulling $3 million worth of advertising from the magazine. Maya decides to try and get the advertising back herself, without help. Meanwhile, Jack helps Elliott with his new girlfriend. Jack sends Elliott's date poems, flowers and much more in Elliott's name. She ends up dumping Elliott because "he" was smothering her.

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.

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.

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.