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).
Jack and Finch prepare for a meeting with Tate Gittling (guest star Alan Rachins, ""L.A. Law""), 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.
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.
Gina Gershon guest stars as Rhonda, the beautiful but foul-mouthed sister of Vicki who immediately falls for Elliott. But when Elliott feigns interest in Rhonda only to ultimately make himself seem more interesting to Vicki, he finds himself in an awkward situation and only Finch can save him. Meanwhile, Jack annoys the entire office when he sets up closed-circuit cameras everywhere in an attempt to keep his eye on everyone while is home recovering from foot surgery.
Jack hires a woman off the street to run the desk. The staff thinks its because Jack wants to seduce her. This causes her to quit. When the staff finds out that Jack didn't hire her for that reason, they convince her to come back to work. Meanwhile, Finch tries to get a distraught female co-worker to take comfort in his arms.