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.

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.

The gang gathers for Thanksgiving at Jack's mansion in the Hamptons. Nina is convinced that Jack will fire her for being unhip. Jack sleeps with Elliott's mom, but Finch is convinced that Jack did the dirty deed with his date instead. And Maya just wants to put the perfect dinner together.

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.

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.

Elliott doesn't want to tell the office about his new relationship with Maya, while she is quite anxious to. They try to keep it quiet, but everybody quickly finds out.

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.

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."

Jack returns from China with exotic and mysterious candy that has strange effects on the staff.

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.

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.

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.

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 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.

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 goes undercover at a high school and winds up becoming incredibly popular, and having the head cheerleader ask him to the prom. Jack discovers that the office mail guy is an incredible opera singer. Nina becomes celibate, following some advice from Elliott. Nina and Finch kiss.

Finch is banished to the mailroom after insulting Jack. Elliott tries to prove that Maya's hunky gynecologist is a frequent visitor to strip clubs.

Elliott plans to propose to Maya on her birthday. Nina is being honored in her hometown in Kansas. However, after Nina's plans are cancelled, she interferes with Elliott's plan by tagging along to dinner with him and Maya. Elliott manages to propose, but immediately has second thoughts.

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 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.

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.

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!

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.