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 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.

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.

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.

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

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.

Maya discovers that organizing a birthday party for Nina is no cause for celebration.

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.

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.

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.

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

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.

Nina begins dating an actor who lives with his overprotective mom. Elliott reveals a secret to Maya, who promptly tells the entire office.

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.

Finch schemes to hire a sexy au pair to care for his nonexistent son. Elliott and Jack have trust issues after Jack gives Elliott a loyalty test.

Jack takes a vacation and uses the time to fulfill his dream of writing a novel. But when he gets frustrated, he pays an English professor to write the book for him. Meanwhile, Maya, Elliott and Nina are left to oversee the magazine and can't agree on even the smallest decisions.