Nina dates a rock star and tries not to sleep with him on the first date. Maya tries to get Vicky to open up about her broken marriage. Jack gets a pocket watch, and gifts Elliott with a wristwatch to persuade him to stop using his own pocket watch.
Nina throws an A-list Halloween party and reluctantly invites the Blush team. Jack and Finch fight for the affections of a new model with Jack trying to use magic to win her. Maya helps Elliott realise that the only reason he keeps arguing with Vicky is because he likes her. Nina becomes jealous of her new boyfriend Simon and one of his old lovers.
Jack goes on a diet, but Finch keeps feeding him fatty foods so stops being cranky. Vicky's husband returns to beg for her forgiveness and Maya finds herself very attracted to him. Elliott helps Nina make Simon jealous with an incriminating photograph.
Maya helps Finch write a poem so he won't flunk out of college. Jack is impressed by the poem and rewards Finch even though Maya is responsible for it. Nina gets a chance to model again for Vicky's new idea for an article, which brings out a terrible side in both her and Elliott.
Finch tries to get Jack to let him come to dinner with George Lucas. Elliott becomes extremely arrogant when one of his artistic photos is published in a photography magazine. Vicky and Nina are forced to work together on a project, Finch convinces Nina that Vicky is a lesbian and has feelings for her.
Vicki reconciles with her former husband Pete. But he seems confused because he also has the hots for Maya. Finch invents a fictional employee in order to obtain a company parking spot.
Finch begs Elliot to introduce him to the centerfold model Lily Barton, who was his fantasy when he was a teenager. Nina and Simon discuss moving in together while he bonds with Jack.
After Red Finch is forced into early retirement, Finch gets him a job as Jack's driver. Elliott wants revenge after stand-up comic Chick Rivers targets him at a club, and asks his uncle to help with his vast collection of one-liners.
Finch and rival publisher Tate Gittlin's assistant Bridget Manning have a romance, but she has a motive for accepting Finch's advances. Nina is jealous of her musician boyfriend Simon Leeds' celebrity status.
Simon is prepared to ask Nina to marry him, but she's been married for 8 years to flaky Roland Devereaux and asks Elliott for moral support in asking for a divorce. Jack finds a perfect guy for Maya, but she falls for someone else.
Elliot joins a Bible reading group and fantasizes about the women there. Finch also joins the group and discovers these women aren't so celibate after all.
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.
Finch and Elliot become rivals over a mutual male friend whom they both have an emotional connection with. Nina's dead friend Binnie shows up in her dreams.
