Nina starts dating a British rocker named Simon Leeds. Meanwhile, Maya convinces Vicki to give her the details of her divorce. And Jack is prancing around showing off his new pocket watch until Elliot gets one too.

Nina is throwing a Halloween party! At the party, Finch and Elliot compete for Blush's newest cover model, Kelly. In the end Finch gets her, only to find she is a lesbian who thinks he is a woman. Meanwhile, the jealous Elliot tries to keep Vicki from going home with a guy she met at the party.

Passion enflames Maya, drawn to a fireman hunk who's Vicki's estranged spouse; jealousy rages between Nina and her rocker beau.

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.

Finch forgets to tell Jack about an important meeting with foreign clients, so he assumes Jack's identity and attempts to close a deal without Jack's knowledge. Meanwhile, Nina and her rock star boyfriend Simon (guest star Simon Templeman) force themselves to go clean in an attempt to get Nina's hard-partying granddaughter (guest star Sasha Barrese) to change her ways, and Elliott seizes an opportunity to confront his high school bully (guest star Jason Marsden).

Rivalry over a charity event leads to tension between Jack and a fellow magnate (Alan Rachins), whose comely assistant gets hot and heavy with Finch.

Jon Lovitz portrays Nina's estranged, foppish husband, who still enthralls her. Elsewhere, Maya's swept away by an environmentalist (Stephen Dunham) her father dislikes.

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.

Nina feels threatened by Skyler, an old fling of Simon. Skyler would be the minister at their wedding reception. Jack and Finch scam to get rid of her. Meanwhile Maya has found the perfect man, who turns out to be a senior in High School.

A boycott of Blush is threatened by a feminist, whom Jack uncharacteristically finds "very interesting [and] attractive". Also: a male-bonding feud pits Finch vs. Elliott; and dreams of infidelity haunt Nina.