Out of work and out of money, Maya is forced to ask for a job from the one person in the world she least wants to work for- her father Jack. When she gets there, she has to face some unexpected competition from Jack's current employees: fashion editor Nina, who fears Maya will squeeze her out of her job, secretary Finch, who fears Maya's presence will diminish his influence with Jack, and head photographer Elliott, who hates having to put up with Maya's resentment of his attitude toward women. The biggest obstacle of all proves to be Maya's own pride and her hatred of all Jack and Blush stand for.
Maya begins work at Blush. Jack welcomes her to the office by showering her with a ton of gifts and presenting her with a great new office, complete with the best in office accessories. Maya is completely caught up in the thrill of it all until she discovers the reason her father is doing it- to distract her from her plans to change the magazine.
Fed up with Maya and Nina's constant bickering, Jack asks Maya to throw Nina a birthday party as a goodwill gesture. Maya tries her best to be nice, but Nina's relentless barbs push Maya to her limits. Also, Finch claims that Elliott's success with women is entirely due to his glamorous job, so he comes up with a bet to prove it: Elliott must pick up women, same as always, except he must do it under the pretense of a different job title assigned to him by Finch.
Appalled at how bad she looks in her current ID photo, Maya agrees to let Elliott take a new photo of her which will make her look more attractive. Unfortunately, Elliott makes her look a little too attractive. A racy dream that ensues only adds to the trouble. Meanwhile, Finch power trips big time by writing a lengthy new office policy which seems to serve his own interests more than those of the office.
Jack returns from his trip to China and he brings back gifts for everyone, including a strange candy called Lemon Wacky Hello. The Hello proves to be very wacky indeed, as it contains a hallucinogenic drug that puts everyone into an acid-trip-like state and disrupts Maya's first chance to put the magazine together by herself.
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.
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 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.
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 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.
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.
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.
Finch and Adrienne return from a wonderful honeymoon in Tahiti, but upon their return, Finch is hit with a hard dose of reality. If he is to maintain his "cool" image in Adrienne's eyes, he will have to give up a lot of his favorite things, such as action figures, sci-fi conventions, and cat shows. What makes this so problematic is that his cat Spartacus has just made the finals of a big cat show, and winning has been a lifelong dream of his. Meanwhile, Maya and Elliott fret over whether their marriage is legal or not and end up seeking out the help of the cult's strange lawyer, Larry. Larry successfully annuls the marriage, but the two are left still unsure about the possible future implications of the whole affair.
A planned Blush article on lost loves leads everyone to reminisce about their own lost loves. The saddest story belongs to Elliott, who saw his dream girl sail out of his life when a hit and run driver knocked him down on his way to propose to her. The story has an extra meaning for another person, however. When Elliott describes the incident, Nina realizes that she was the driver in question. Meanwhile, Finch wants desperately to convince the world that he is actually married to Adrienne, so to help him out, Jack takes out a big wedding announcement in the New York Post. Unfortunately, the attention it draws is of the unwelcome variety: an INS agent arrives at the office charging that the marriage is a sham. And why does it matter what the INS thinks? Because it turns out that Adrienne is actually a Canadian citizen whose work visa has just expired.
Finch is upset because Adrienne is in Europe modeling and it's his first weekend away from her. Maya tries to convince Nina that the moon landing wasn't a hoax. Elliott is blackmailed into hiring a sleazy photographer as his assistant because the guy has a picture of Elliott having sex with Adrienne.
Finch tries to find a new model girlfriend. Maya and Elliott try to decide what to do about their kiss. Maya proposes a dinner "meeting" since neither of them can bear to call it a date. Meanwhile, Maya's former assistant Cindy visits; she's now a media buyer. Jack makes Maya take Cindy out to dinner and Elliott goes along so that it really is a meeting. Elliott and Maya drink too much and Elliott wakes up with Cindy and must find a way to tell Maya. Part two of two.
Jack and Maya run into his ex-wife Roberta on an airplane to Paris. Jack desperately tries to convince her to marry her new boyfriend so he can stop making alimony payments. Finch and Elliott convince Nina that Jack is still in the office, until she discovers their prank and enlists Kevin the mail guy to help get them back.
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.
Nina reluctantly meets with her former agent, Catherine. Catherine wants Nina's help with a suicide attempt. But after she becomes friends with Finch, she decides that a night of sex with him would be the best way to go out. Meanwhile, Maya thinks her new boyfriend likes his woman heavy and is trying to fatten her up.
A few weeks have passed since Elliott and Kaylene started dating, and the two are starting to get extremely close. A little too close, as far as Elliott is concerned. Things are moving very quickly between them, and Elliott just doesn't feel like he can commit that deeply to her. He and Maya start chatting about it in his studio one night, and instantly, the spark between them returns. Before they realize it, Maya and Elliott are finally sleeping together. Maya wastes no time in chastising herself for it the next day. She claims that Elliott sleeping with her was only the result of his fear of committing to Kaylene, and that she now occupies a position she had previously treated with scorn and ridicule -- that of the "other woman". Elliott doesn't see it that way. He tries to tell her so, but she won't listen. He finally breaks things off with Kaylene, explaining that he's in love with someone else, and that even though that someone won't have him, he can't go on seeing Kaylene feelin
While attending one of Nina's sex addict therapy sessions, Finch overhears ex-wife Adrienne telling the story of a recurring fantasy: Finch in a pirate suit. He soon sneaks into her apartment to try it out, only to discover her new boyfriend: a cop. Meanwhile, Elliott and Maya struggle against Jack's intimidation to buy cookies for his daughter's private school.
Jack worries over what to get Donald Trump for his birthday; the two share the same one and Trump always gets him a better gift. Finch breaks the "assistant's code" when Jack presses him for information on the gift. Meanwhile, Maya and Elliott search for a couple who shares their interests. The couple they meet, however, misinterprets their offer to go swing dancing.
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.
"Nina Van Horn: Trouble Be Thy Name" features clips from her blaxploitation movie "Foxy Trouble" with Bernie Casey, her discovery as Claire Noodleman, interviews with her co-workers, her disastrous month-long marriage to Robert Evans, her fiery time with a cult, her involvement in the closing of Studio 54 and her mark on pop music, among other things.
Maya is reunited with her best friend in high school, Alan, who is now a successful motivational speaker. However, Alan confesses to Maya that he is a recovering alcoholic, but another revelation causes the trouble: he was responsible for her school shunning her. When Maya is unable to forgive him for this, he begins drinking again, disrupting the motivational talk he is to give at the Blush office. Meanwhile, Jack is frightened because of a recurring dream he has about Kevin.
Maya gives Elliott the ring back. Elliott proposes again and passes out again. Maya comes to the realization that Elliott is not interested in what she is and kicks him out of their apartment. Meanwhile, Finch discovers that a porno was shot in Jack's office. After discovering that Nina may be the one behind it, he uses her contacts to get a script of his made.
Jack doesn't like Finch's gift of dog tags. Nina hooks Elliott up with a "friend" for Jack's charity auction after he discovers that Maya has a date already. The "doctor" turns out to be an illiterate hooker. Finch, acting as auctioneer, tries to undermine the auction when he discovers that Jack threw his gift away.
Finch is DJing a bar mitzvah. Nina is tricked into attending by the man of honor who has the hots for her. Even after Sid's plan is uncovered, Nina agrees to stay and deal with Sid's advances because Finch leads her to believe he's dying of a rare disease. Meanwhile, Jack and Elliott aggravate Maya when they flip-flop their desire to date a woman based on whether or not they think the other one wants her.
Jack discovers Finch and Allie; he fires Finch the next morning. Two weeks later, Jack has a new secretary, for whom Elliott and Nina cannot decide their feelings for. Finch wants to come back, but finds a job as Snoop Dogg's assistant when Jack refuses. After Allie tells Jack the truth about how she came onto Finch, he decides that he wants his old assistant back.
Jack hires Betsy Frayne as the new security officer for the office, and Finch freaks out. Betsy went to college with him, and Dennis says she stole his personality. The Blush staff has Betsy thrown out of the building and fired, and are about to call the police when Dennis admits that he was the one who stole her personality back in college. Betsy is rehired, and now Dennis has to find another personality or settle with his dull (but true) personality, Denny, while Betsy confesses her true intentions of seducing Dennis. Meanwhile, Elliot forbids Jack from eating his cannolis after Maya and Nina accuse him of being Jack's bitch and Jack decides to get back at Elliot using his social influences, until Elliot can't take it anymore and gives Jack his last cannoli.
Elliot encourages Dennis to give Betsy a chance, since he thinks she's perfect for him. Although reluctant at first, Finch finally gives in and discovers the wonders of being in a healthy relationship. That is, until Betsy makes an inadvertent move on Elliot and proposes a threesome, which freaks Finch (and Elliot) out. Meanwhile, Maya struggles with the possibility of her father giving her special treatment when she asked for a raise and pretends she is leaving the magazine.
Nina's long time friend Binnie unexpectedly dies, and Nina has a hard time dealing with it until Elliot confronts her. From ignoring her death, Nina takes a weird turn to worshiping and hanging out with her urn, until she loses her friend's ashes. Meanwhile, Jack has a new pet: a mini-computerized egg that will do almost everything Finch does, causing him a great deal of jealousy. Finch then decides it's time for him to do something that will take him to the higher steps of life and go to college – through the Gallo Foundation Scholarship, that is. Unfortunately, Maya is there to bring the good sense down to her father, and he ends up giving the scholarship to someone who really deserved it: the eastern European cleaning lady's grandson.
Maya is looking for a new assistant and thinks she's found the perfect one when Amy Watson, a good looking, young and intelligent woman shows up at the office. The entire male staff of Blush is drooling over her, and Nina warns Maya about Amy, but she thinks Amy is not just another dumb blond bimbo. Amy tries to show Maya some articles she has written, hoping that they would end up published in the magazine, but Maya thinks their content doesn't go with the Blush's theme. Nevertheless, Amy goes over Maya's head and shows the articles to Jack, who makes her Blush's newest sex columnist. Maya, who was just convinced to fire her because Amy was not at all what she thought, is shocked. Meanwhile, Elliot finds himself in an awkward position after setting Kevin up with a woman.
Finch and Elliot are fighting over Amy. Jack warns Amy that the fight is interfering with the office work environment, and so Finch and Elliot come to terms about Amy: they decide that since they both like her so much, they should share her, meaning she would spend half her time with one and then the other half with the other. Of course Amy is not ok with that and decides to quit the magazine altogether since she got a six figure book deal. Meanwhile, Jack and Nina try hard to show Kevin the good of being rich and end up corrupting him. Now Kevin, who was once happy and simple, is miserable and full of debts.
Nina is tired of Kevin's obsession with her and his sick, weird gifts, so she asks Maya to tell him to back off. Maya agrees, but assures Nina that Kevin is just a sweet guy and not the weirdo she thinks he is. Later that night, Maya is surprised at her building by Kevin and gets a little freaked out. Her suspicions come true the next morning when Kevin tries to return a quarter she dropped while entering the lobby. Maya yells at Kevin, who runs away shocked to discover everyone thinks he's a pervert. Maya sends Nina to talk to him, and Kevin confesses his feelings for her and asks for a kiss, which she reluctantly agrees. Surprisingly, he kisses her forehead. Meanwhile, Jack has to suck up on an arrogant millionaire so he can launch a Blush channel on cable, and tries to bribe Elliot so he can be laughed at and made fun of by the millionaire. But Jack is forced to interfere when the guy crosses a line with his friend.
It's Christmas time and Jack throws his annual party at the office. He dresses up as Santa, and tells Elliot's nephew that he won't get any presents for being a naughty boy and pushing Hannah out of the line. When Jack finds out the truth that Hannah made it up because she thinks she can do anything and her daddy owns the world, he has to apologize to little Paul, but only make things worse. Meanwhile, Kevin's cousin Ray Liotta attends the party and sparks fly between him and Maya. But Ray's odd obsession with Christmas scares her away. And Finch and Nina fight over who creates the best new Christmas song. They can't come up with anything so they decide to become Jewish.
Jack challenges Elliott to a game of darts and hits him in the back when Elliott accuses him of being too competitive. Meanwhile, Nina reveals that she had a daughter 34 years ago that she gave up for adoption, and her daughter is trying to find her. Nina enlists Finch to pose as her "son" but when she tells her daughter the truth, she wants nothing to do with her. Trying to make amends, Nina discovers that she is a grandmother also.
Nina is trying so spend some quality time with her granddaughter Tess. Chloe asks Nina to keep Tess from bars, boys and clubs, but all Tess wants is to get wild. She throws herself at men at a bar and later at Finch, who pretends to be the magazine's editor. When Tess runs away, Chloe and Nina find her at Dennis's, and they all offer to sleep with him in order to keep Tess from doing so. Meanwhile, Jack insists on giving Maya a birthday present, but has no luck with his ideas or Elliot's. She gets mad not because of the meaningless gifts, but because it's really not her birthday and her father should know better. Still, they both feel like it's someone's birthday – and it is: Maya's mother!
Ray Liotta appears on "The Tonight Show," pledging his love to Maya. She rejects him until he agrees to give up being in the public eye for her, although he finds it difficult to adjust to being a regular guy. Elliott and Finch play a joke on cocky Jack, who has bought a desk once owned by George Washington. And Nina creates a one-woman show based on her life.
Nina dumps a blind man named Jay, whom Maya feels sympathetic for. Jay asks Maya out for a date at the movies, which she thinks at first to be a nice and interesting experience. But her opinion quickly changes when she discovers that Jay tends to lash out his anger publicly. She tries to dump him, but he convinces her that he'll behave. He comes over to her place to watch some more movies, but Jay brings porn and Maya kicks him out for good. Meanwhile, Jack encourages Finch to take some useful classes in college, so Dennis takes on TV Production. He starts his own show - "Finch Attack!" - and asks Elliot to be his first guest. Halfway through the interview, he literally attacks Elliot and tapes him to the chair. After apologizing, Dennis convinces Elliot to help him attack Jack, but instead they both attack Elliot again.
Trying to find a photo for a show, Elliott chooses a nude photo of Maya he took when they were dating and she passed out drunk. Jack hires a tutor for Finch, although she turns out to be a massage therapist as well. When Finch confesses he got a massage instead of being tutored, Jack is happy because Finch is maturing.
In a satire of "Project Greenlight," Finch makes a ten-minute semi-autobiographical movie for his film class, and convinces actor David Hasselhoff to play the father in the film. But when filming starts, trouble ensues when Nina, playing the mother, falls in love with the actor playing her son. Meanwhile, Jack demands an onscreen apology from Hasselhoff after the actor scratches Jack's car in the parking lot.
Elliott becomes distraught when his grandmother becomes more interested in spending time with Finch than her own grandson. Meanwhile, Maya wants to bring a little patriotism to the Blush office with small American flags for everyone, but Jack decides to make a grander gesture, with disastrous results.
Jack hires a woman off the street to run the desk. The staff thinks its because Jack wants to seduce her. This causes her to quit. When the staff finds out that Jack didn't hire her for that reason, they convince her to come back to work. Meanwhile, Finch tries to get a distraught female co-worker to take comfort in his arms.
Gina Gershon guest stars as Rhonda, the beautiful but foul-mouthed sister of Vicki who immediately falls for Elliott. But when Elliott feigns interest in Rhonda only to ultimately make himself seem more interesting to Vicki, he finds himself in an awkward situation and only Finch can save him. Meanwhile, Jack annoys the entire office when he sets up closed-circuit cameras everywhere in an attempt to keep his eye on everyone while is home recovering from foot surgery.
Finch forgets to tell Jack about an important meeting with foreign clients, so he assumes Jack's identity and attempts to close a deal without Jack's knowledge. Meanwhile, Nina and her rock star boyfriend Simon (guest star Simon Templeman) force themselves to go clean in an attempt to get Nina's hard-partying granddaughter (guest star Sasha Barrese) to change her ways, and Elliott seizes an opportunity to confront his high school bully (guest star Jason Marsden).
Finch's old buddy Bert - now a transsexual named Brandy - joins Finch as a couple at their high school reunion in order for Finch to arrive with a beautiful blonde while Bert/Brandy can attend without revealing his true identity. At the reunion, the girl they both competed for in high school hits it off with Brandy and reveals her past crush on Bert. Meanwhile, Maya and Elliott decide to become intimate with no strings attached.
Jack and Finch prepare for a meeting with Tate Gittling (guest star Alan Rachins, "L.A. Law"), the publisher of Blush's biggest rival magazine, in an attempt to join together for a charity function. But when Finch becomes romantically involved with Gittling's assistant, Bridget (guest star Judy Greer), he drops his guard and she sets him up to make Jack look bad. Meanwhile, Nina becomes jealous of her rock star boyfriend's (guest star Simon Templeman) celebrity status.
Simon (Simon Templeman) is about to pop the question to Nina (Wendie Malick), but she panics when she has to tell him she's still married to her last husband - the enchanting Roland Devereaux (guest star Jon Lovitz, NBC's "Saturday Night Live"). Jack (George Segal) finds the perfect man for Maya (Laura San Giacomo) - his lawyer - but Maya sticks to her instincts and falls for a radical naturist. David Spade and Enrico Colantoni also star.
At Vicki's suggestion, Jack asks all the Blush staff regulars to anonymously evaluate his work. Finch, Nina, Maya, and Elliott submit signed appraisals that only include words of praise, while Vicki anonymously tells Jack the truth. By process of elimination, Jack knows who the criticism came from, and he is spurned. Vicki consoles him and finally convinces him that the truth is healthy. Jack then insists that everyone tell him something honest, which sends Finch into a tailspin of vitriolic criticism. Meanwhile, Nina sprains her ankle after Maya suggests she walk somewhere, and Maya has to take Nina's place at a fashion event. When Maya has a great time, Nina becomes jealous.
The series won't be returning in the fall, but tonight NBC unreels two first-run episodes that showcase the sly repartee and gleeful double entendre that became the show's hallmark. First up, hairstyling once again occupies Vicki (Rena Sofer), who's "dyeing" to give Blush the brush; Nina takes under her wing the female impersonator who's portraying her in a cabaret show; and Dennis rides roughshod over his new assistant---Elliott.