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.
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 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.
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.
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.
Finch takes the news of the engagement quite badly. Not only is he concerned for his father's well-being, the prospect of having Nina as his stepmother terrifies him. However, when a night of passion puts Red in the hospital, it causes him to seriously question his impending marriage. After a heart-to-heart with both Red and Nina, Finch finally convinces both of them to call it off. Meanwhile, Elliott miraculously gets another chance with Tyra Banks, but once again, Jack accidentally screws things up for him.
Maya's attempt to host a murder mystery party is plagued with problems. Elliott wants to ditch the party for an Armani gala being held on the same night, Nina shows up with Maya's old boyfriend Derek, Jack wants to wear Elliott's costume, Finch is trying to make time with the caterer (who is dressed as a large-bosomed French chambermaid), and gamemaster Larry is a down-on-his-luck actor who spends most of the party on the phone with his agent. Everything is thrown into chaos when Maya's next door neighbor suffers a heart attack and drops dead -- and everyone but her thinks it's part of the game.
As a prank, Finch switches the cards on two of Elliott's birthday gifts: those from Maya and Persky. As a result, Elliott believes that Persky has given him a really cool video game system, and Maya has given him a box of kinky sex toys. When Maya invites him over that night to have some fun, he naturally gets the wrong impression, and is forced to give his relationship with her some deep thought. Meanwhile, when the racehorse Jack bought with Robert Goulet acts up before the big race, he enlists Nina's aid to calm it down.
Maya decides that since the new Miss Pretty column is so good, she will do a column on Miss Pretty. Finch then informs her that the new Miss Pretty is actually a man, but Maya thinks that will make the article even better, and insists on meeting him. The trouble is that Miss Pretty is actually Finch himself-and he is determined to keep the office from discovering it. He tries to escape from the mess by hiring professional scam artist Kurt to pose as Miss Pretty, but things only get worse when Maya falls for him. Meanwhile, Nina finds herself roped into an unwanted friendship with a woman she can't stand, and Elliott and Jack find themselves in hot water when they accidentally insult an Asian-American executive from an important advertiser
Maya's enrollment in a photography class causes problems on multiple levels between her and Elliott. Elliott takes an immediate dislike to Maya's teacher, Martin Spancer, when he insults Elliott's work for being too commercial. Then when he assigns Maya to do a nude self-portrait, Elliott claims that he only gave her the assignment so that he could see her naked body. Believing that Elliott's accusation is based on his personal dislike for Spancer, she disregards him. However, when Spancer raves about her nude photos and invites her to go away with him for a special weekend session, Elliott becomes even more convinced that his intentions are purely sexual. Meanwhile, Finch becomes extremely jealous when Nina's new assistant Brad begins entertaining Jack with magic tricks.
The nominations for the annual Femmy awards are in and Maya, Nina and Elliott are nominated, while Finch isn't even invited to the ceremony. Jack switched Maya's nominated article and nominated a picture of Elliott's that was actually taken by a chimpanzee. At the dinner, Finch scores a seat at the models' table while Maya and Nina prepare speeches. Elliott is going crazy with guilt until he loses. Nina wins after 12 straight years of losing. Maya wins for the article, which Nina trashed in her acceptance speech.
The staff prepares for the annual softball game against the magazine Cosmo. Jack hires Steve Garvey, so that he can play on the team. Maya turns out to be a great pitcher but becomes too competitive.
Jack vows to get in shape after throwing his back out playing with Hannah and hires a personal trainer who used to be a Navy SEAL. Meanwhile, Finch and Maya collaborate on a screenplay, leaving Elliott out in the cold.
After yet another relationship goes sour, Nina realizes that her lack of romantic success is probably due to her tendency to make bad choices in men. Her resolve to start making good choices is tested almost immediately when her old boyfriend Roy breaks out of prison and she falls in love with and begins dating not only Roy, but also the cop who is pursuing him. Meanwhile, Jack, Finch, and Elliott engage in a series of wagers on how predictable each other's behavior is.
Finch is very frustrated when an old nemesis, Barry, shows up one day to gloat over his success. Not only does Barry own a successful business, but he is also engaged to their high school homecoming queen. Finch agrees to a double date with Barry and his fiancée, and he wants desperately to show Barry up by scoring a better looking date. He finds his answer in the form of Adrienne, a gorgeous supermodel. Adrienne would normally be way out of Finch's league, but by manipulating her many insecurities, he makes her fall for him. However, he still has one more obstacle to overcome: Adrienne's ex-boyfriend has decided he wants her back. Finch is forced to take desperate action if he wants to hold on to her, and does—he asks Adrienne to marry him, and surprisingly enough, she says yes. Meanwhile, Jack makes plans to have his photo taken in front of a new painting in his office, but unfortunately, he doesn't realize that the painting depicts an obscene act.
Finch announces the engagement at the office, but it takes several minutes to make everyone believe it. When they finally do, though, it begins a heated argument between Maya and Elliott over whether Finch's and Adrienne's love is for real. It may not matter either way, though, because once the news of the engagement spreads, Adrienne's ex-boyfriend Brian shows up at Blush with plans to beat up Finch. Finch manages to avoid Brian temporarily, but the incident forces him to speed things up yet again-with a wedding that very day. Finch and Adrienne are married after Brian punches Finch. But...Elliott and Maya are also married while looking for Finch in a mass wedding.
