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.

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.

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.

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.

Finch tries to fix his visiting mother up with Jack, in hopes that he can become a Gallo. Elliott tries to help a photographer find his passion.

Nina talks Maya into dating a handsome but dumb exterminator. Maya is tested when she meets a smart man at an art gallery and sleeps with him. Meanwhile, Jack tries to teach Elliott and Finch a lesson when they begin paying Kevin to eat weird things.

After the staff embarasses themselves in front of designer Kate Spade, Jack hires a corporate therapist.

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.

Jack and Finch prepare for a meeting with Tate Gittling, 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.

Magazine owner Jack Gallo makes peace with his estranged daughter when she asks him for monetary help--and lands a job at the mag.

On her first day at work, Maya decides to do a hard-hitting story on child labor overseas, while Jack tries to distract her with a plush office.

Dennis experiences an identity crisis on Secretary's Day, while Nina tries to lift her spirits.

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.

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.

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.

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.

Nina and Finch don't know about Jack's divorce yet. Jack moves into the Plaza Hotel for privacy. Maya wants Elliott to read an article about relationships but he doesn't, which causes problems. Everybody gathers in Jack's room. Finch and his singing group, 2 Fine, perform.

Finch's old friend Bert visits with surprising news--he is now a sexy woman named Brandi. This causes problems for Finch when he becomes attracted to Brandi. Meanwhile, Elliott tries to get Nina to be nicer to her assistant.

Finch dates a female boxer with a jealous ex-girlfriend. Elliott, Jack and Nina fool Maya into believing that they're smarter than she is.

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.