Determined to prove that good-looking people have an unfair advantage in the job market, Maya concocts an experiment. She'll send two people to interview for the same job- one is unattractive but perfect for the job; the second has the brains of a Stegosaurus but is gorgeous. She soon falls victim to the very prejudice she is trying to fight when she and the good-looking guy start dating. Also, Nina begs for the chance to participate in an office prank on Finch while Jack struggles with the complicated assembly instructions to his baby daughter's dollhouse.

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 Maya scores an interview with legendary rocker Nick Hewitt, a flood of memories is triggered for Nina of the affair they had 25 years ago. Nina describes it as the most romantic weekend of her life, and she realized he felt the same way when the song ""Nina in the Cantina"" hit the charts a few months later. Unfortunately, Maya learns that the song was actually about Twiggy, and Hewitt only used the name Nina for the purpose of the rhyme. Worse, he doesn't remember Nina at all, leaving Maya to engineer a big charade to keep Nina from getting hurt. Meanwhile, Elliott's extreme jealousy of Annie Liebowitz is exploited everywhere he turns, while Finch tries desperately to get rid of an ugly handmade vase given to him by Jack.

It's a day to celebrate for Nina- her famous bikini is about to be put on display in the Model Cafe, a sort of Hard Rock Cafe for supermodels. Her mood turns from celebration to despair, however, when she finds out exactly where in the cafe it is being displayed- over a dumpster. Finch and Maya, concerned over their friend's feelings, conspire to steal it back for her. Meanwhile, Jack has Elliott take boudoir photos of him as an anniversary present for his wife, but neither model nor photographer is without reservations.

Maya and Finch attend designer Oscar Milos's fashion show using Nina's tickets. At the party, a drunken Maya makes some caustic remarks to a newspaper reporter, resulting in Milos pulling $3 million worth of advertising from the magazine. Maya decides to try and get the advertising back herself, without help. Meanwhile, Jack helps Elliott with his new girlfriend. Jack sends Elliott's date poems, flowers and much more in Elliott's name. She ends up dumping Elliott because ""he"" was smothering her.

Maya becomes smitten with a United States Senator, but loses him to Nina through a series of deceptions on Nina's part. Nina convinces him that she is an old-fashioned Southern belle with no vices whatsoever, and that Maya is a drug addict. Also, when it is revealed that Elliott stole a Six Million Dollar Man doll as a kid, he becomes racked with guilt over it while Finch can only think of the potential collector's value of the item. Finally, Jack decides to see what life is like from his employees' point of view and moves his desk into the center of the office.

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