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 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.

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.

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 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.

Adrienne's hand-model friend tries to make Finch look like a jealous husband. Nina does community service.

Finch is in denial about his divorce and Nina's reporter friend wants to turn it into a major news story. Elliott introduces his visiting lumberjack friend to Maya and becomes jealous when they hit it off. Maya and Elliott kiss. Part one of two.

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.

Nina is dating the lead guitar player of Finch and Kevin's new ""air band"" and convinces him to quit the group. Meanwhile, Jack's rivalry with Alan Thicke drives both of them to therapy with their daughters.

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.

Finch is scared about Jack liking Vicki, so he sets her up to look bad, but he's not sure when she'll get him back. Meanwhile, Nina brings in a woman off the street to prove to Jack that he was wrong to hire Vicki. She is worried though when the woman gets lost in the building.

Nina starts dating a British rocker named Simon Leeds. Meanwhile, Maya convinces Vicki to give her the details of her divorce. And Jack is prancing around showing off his new pocket watch until Elliot gets one too.

Nina is throwing a Halloween party! At the party, Finch and Elliot compete for Blush's newest cover model, Kelly. In the end Finch gets her, only to find she is a lesbian who thinks he is a woman. Meanwhile, the jealous Elliot tries to keep Vicki from going home with a guy she met at the party.

Rivalry over a charity event leads to tension between Jack and a fellow magnate (Alan Rachins), whose comely assistant gets hot and heavy with Finch.

Jon Lovitz portrays Nina's estranged, foppish husband, who still enthralls her. Elsewhere, Maya's swept away by an environmentalist (Stephen Dunham) her father dislikes.

Elliott's duplicitous brother (David Cross) returns, accompanied by his fiancée and now deeply sorry for conning his sibling in the past. The sudden turnaround doesn't convince Elliott, who's determined to prove this is another scam.

The outrageous behavior between Finch and his sexy partner (Gina Gershon) galls Maya, who sets out to rein in the stallion. Also: Jack and Maya compete for an office-cleaner's favor in a feud that gets way out of hand.

The outrageous behavior between Finch and his sexy partner (Gina Gershon) galls Maya, who sets out to rein in the stallion. Also: Jack and Maya compete for an office-cleaner's favor in a feud that gets way out of hand.

Richard Kind ("Spin City") plays a boorish intern at Blush with a crush on Maya. Also: Elliott is drawn to the women at his Bible-study class that's crashed by lascivious Finch, passing himself off as a sinner anxious to be saved.

Nina feels threatened by Skyler, an old fling of Simon. Skyler would be the minister at their wedding reception. Jack and Finch scam to get rid of her. Meanwhile Maya has found the perfect man, who turns out to be a senior in High School.

The series finale centers on a send-off for retiring Jack, whose staffers share memories, shed tears and pay affectionate tribute. Finch puts his feelings into rap, while Nina likens Jack to---what else?---"a perfect glass of Scotch."

Staff critiques vex Jack, who demands honesty and gets it, especially from servile Finch; a role reversal with Nina makes Maya a partygoer.

Vicki's back in the hairstyling biz and is now dyeing to give Blush the brush; Nina takes under her wing a female impersonator who's going to portray her in a cabaret show; and Dennis rides roughshod over Elliott, his new assistant.

A boycott of Blush is threatened by a feminist, whom Jack uncharacteristically finds "very interesting [and] attractive". Also: a male-bonding feud pits Finch vs. Elliott; and dreams of infidelity haunt Nina.