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.

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.

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.

While writing his memoirs, Jack suddenly contracts a horrible case of writer's block. He then realizes why- he has come to the place in his memoirs where he fired his old partner Herb just before Blush took off. Discovering that his old partner has been toiling in a toyshop in Connecticut for 30 years earning a meager living only worsens the guilt. In an attempt to make it up to him, Jack gives Herb a high position in the magazine only to rediscover the reason he let Herb go in the first place- Herb is terrible at the magazine business. Meanwhile, Nina's problems with an IRS audit seem to be over when the female auditor takes a liking to Elliott, but in fact, they're just beginning.

Maya senses trouble when Nina proposes a double date for the two of them. She is proved right when her date, after throwing his back out in her apartment, is revealed to be a United States Congressman - and a married one. Afraid of a scandal, he forces Maya to harbor him in her apartment while newspapers overflow with news of his disappearance and rumors of where he might be, and his friends, family, fellow Congressmen, and the police relentlessly search for him. Meanwhile, a friendly game of paintball causes a major office tiff when a fear-crazed Finch shoots Jack a few seconds into battle.

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 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.