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.

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.

Finch, desperately seeking an apartment, convinces Maya to move in with Elliott. But when the two fight on their first night together, Finch may be in trouble when Maya returns home and he has a woman in his bathtub. Meanwhile, Jack and Nina argue on the anniversary of their first meeting.

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.

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.

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 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 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.

Jack discovers a young black man masquerading as his son in an attempt to gain important business contacts. Elliott and Nina serve as judges for the Rave TV Fashion Awards, but Elliott becomes dismayed after observing bribery. Maya wants to create a new literary magazine.

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.

Nina discovers that she can overhear Jack's private therapy sessions and blackmails him into using the company limo. Maya writes a story about gambling and goes a little too far.

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.

"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.

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.

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.

Maya and Jack accidentally kill Finch's cat but feel pretty guilty when he has it stuffed and sits it on his desk. Nina's advice to some Nature Scouts causes Elliott's mother to leave her husband.

Finch's former figure skating partner visits and asks for him for help coaching her and her new partner. Maya bleaches her hair as a research project and convinces Elliott to enact some sexual fantasies. Nina worries that an ailing Ed McMahon may cause the preemption of an A&E biography about her.

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.

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

With the Citizens for Morality protesting about Blush's explicit covers, Nina wants to help. Jack turns her down but changes his mind when Nina turns out to know the head of the protest. Meanwhile, Finch goes to bodyguard school and Maya literally drives herself crazy.

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 realizes that he and Adrienne are very different from one another and begins to doubt their marriage. Meanwhile, Jack asks Maya to do the annual employee evaluations.