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.

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.

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 the awkwardness, 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.

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.

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.

Halloween is no treat for Maya when Finch gets her to wear an embarrassing costume to the office. Luckily, she meets her Prince Charming in an elevator. Meanwhile, Jack confesses to a dirty trick he played on a young impressionable Maya; and Elliott and Finch hatch a plan to find out if Nina's friend Binnie really exists. Finally, Finch claims he wasn't the least bit scared by Alfred Hitchcock's horror masterpiece Psycho, so Elliott sets out to prove he's lying.

Finch is convinced that a model likes him, only it turns out that she likes Maya instead. He sets out to create the ultimate male fantasy: watching two females go at it. All is going well for Finch, until Maya finds out and the two females decide to turn the tables on him. Meanwhile, Elliott and Nina go overboard in their insults after Jack tells them that he just wants to be one of the guys.

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.

Maya's coworkers find it strange when she begins dating Steven, the host of a children's puppet show. As far as she's concerned, though, their relationship is going very well--until she suspects Steven is using the characters on his show to criticize her. Meanwhile, Nina decides to enter the entrepreneurial world, but her choice of investments--a nightclub that doesn't even have a name--is questionable indeed. Also, a heartfelt confession of Elliott's (he sometimes wishes he was a woman) during the guys' emotional viewing of Brian's Song comes back to haunt him.

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.

Finch sneaks a look at the office Christmas presents and is disappointed by his when he discovers that it's not what he wanted. So, he sabotages the office Christmas. Meanwhile, Nina learns the true meaning of casual wear, Elliott protests the commercialization of the holiday and Maya rags Jack about his selfishness.

When Maya's first love John Kenny pops back into town, she becomes as happy as she's ever been, as the two find their old spark back in full force. However, Jack is angry about the whole thing, as he still has not forgotten when he walked in on the two of them fooling around one time. Maya then learns the true horror of the situation- the only reason they were separated in the first place was because Jack had pulled strings to get him into the Royal Shakespeare Company, and she becomes instantly fearful that he will once again begin to interfere with their relationship. Meanwhile, Finch uses a ""tough love"" method to train a new intern while Nina's television appearance is ruined when an old allergy acts up.

Maya becomes smitten with a United States Senator, but loses him to Nina through a series of deceptions on Nina's part. Nina convinces him that she is an old-fashioned Southern belle with no vices whatsoever, and that Maya is a drug addict. Also, when it is revealed that Elliott stole a Six Million Dollar Man doll as a kid, he becomes racked with guilt over it while Finch can only think of the potential collector's value of the item. Finally, Jack decides to see what life is like from his employees' point of view and moves his desk into the center of the office.

Red Finch is visiting and Dennis is trying to avoid him because of his father's recent divorce. Elliott is excited about the possibility of working with his crush, Tyra Banks. Red and Nina go out for dinner...and more. Elliott meets Tyra but scares the hell out of her due to Jack's stun gun. Red and Nina announce their engagement. Part one of two.