Mona's music-video shoot for a rapper may end in disaster when he refuses to leave the dressing room—until he meets Dee Dee. While Mona is pleased with the rapper's newfound enthusiasm for the shoot, she soon begins to worry that he's using Dee Dee.

While Mona struggles to find work after poisoning her reputation in the record industry, the reporter whose article got her fired tries to make amends and sets up a meeting for Mona to plead her case to Big Phat Slim Jim, the artist she disparaged, in hopes of getting her old job back. Meanwhile, Mona's family and friends offer their encouragement and support in their own special ways during her difficult job search.

After another failed relationship, Mona decides to focus on her career for a while. She is determined to help Zora, a promising young singer, secure a contract with the record company. Zora mistakes Mona's efforts to boost her confidence for romantic interest and develops feelings for her. She confesses her crush to Adam, who keeps the news to himself so that he can watch the sparks fly. Mona struggles to come up with a way to handle the situation without hurting Zora's feelings. Meanwhile, Dee Dee dates a man who pays way too much attention to her feet.

Dee Dee organizes a singles mixer at a local club. She bristles at Mona's claim that she only dates a certain type of man (well-groomed and upwardly mobile), and tries to prove her wrong by picking up a tough guy named Keno. She takes off with him on his motorcycle and joins him at a bar, where she rides a mechanical bull. She has a good time exploring this new side of herself--until she runs into a very angry woman who claims to be Keno's girlfriend. Mona and Nick crash the mixer and meet up with his ex-girlfriend, Raquel. Mona is disturbed to discover that Raquel is her dead ringer, and fears that Nick is just with her because of the resemblance. Meanwhile, Dee Dee must actually care for Drew herself after firing the nanny. She is mortified when she must turn to Phyllis for help when her son will not stop crying.

Dee Dee assigns herself the task of personally helping Mona get over her break-up with Nick. She spends nearly every minute with her and forces her to attend an exercise class. Spencer and Mona plan to go away on a road trip, but Dee Dee forbids this because she is afraid of what might happen. While having lunch, Mona and Dee Dee run into Phyllis and her boyfriend, Ray. He is a popular local disc jockey whom she met after calling in a traffic tip. Dee Dee invites them to a dinner her parents are organizing in honor of her new internship. Mona finally ditches Dee Dee and goes to see Spencer. They discuss the fact that they are doing well after their break-ups, and how lucky they are to have each other. They begin kissing passionately, but Mona quickly leaves. Dee Dee is horrified, but Mona says that it felt right. Spencer confesses what happened to Adam, who warns him that Mona is still fragile but thinks they would be good together. At Dee Dee's dinner, Phyllis announces tha

Dee Dee is furious to discover that Mona has become friends with Dee Dee's rival, Stephanie Seymour, after meeting her through a work event. Dee Dee insists that Mona should dislike the same people that she does because it is her duty as a sister. Mona tricks the duo into having tea with her in the hopes of getting them to make peace, but things do not exactly go the way she had planned. Meanwhile, a rejected applicant for the talent search refuses to take no for an answer.

Phyllis recruits Mona, Spencer and Adam to help out with a telethon on Mother's Day. Big Dee Dee and Dee Dee also decide to participate. Phyllis grows so frustrated with Big Dee Dee's interference at a pre-telethon meeting that she blurts out that Big Dee Dee was pregnant before she got married. Dee Dee is shocked and hurt by the fact that this was kept a secret from her, while Mona gives Phyllis the silent treatment because she is fed up with her bluntness and inability to keep her mouth shut.

Mona convinces Chase to hire Lorenzo as a pastry chef at City Sonoma. Chase become furious with Mona for not informing him that Lorenzo is her ex-boyfriend. Phyllis is bed-rested after taking a fall in the hallway of her apartment building, which Big Dee Dee and Charles happen to own.