Dee Dee has difficulty finding a job after graduation. After she announces plans to return to school, her fed-up father not only cuts her off, but orders her to pay back all expenses accrued since her 21st birthday. Mona begins dating her handsome and charming new neighbor, Lorenzo, but her insecurities stand in the way of the relationship. Spencer changes his wardrobe in the hopes of getting people to take him more seriously.

After Dee Dee complains about Brett's sexist treatment of her, Charles and Spencer show up at the office to confront him. Their actions backfire, as everyone at the office begins thinking of Dee Dee as a "daddy's girl." Dee Dee, with encouragement from Mona, Phyllis and Big Dee Dee, sets out to prove herself by trying to land a successful athlete who has refused to sign with any agent.

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.

While Chase is out of town on a business trip, Lorenzo shares with Mona that he still has feelings for her. Although Mona remains committed to Chase, she begins to fantasize about Lorenzo. Meanwhile, Dee Dee tries to convince Big Dee Dee and Charles to financially support Adam's new career as a stand up comedian. Big Dee Dee quickly agrees when she finds out she can produce his stand-up set.

Mona discovers everyone is hanging out with Chase behind her back. Gus leaves town, leaving Brett in charge of the office. But when Dee Dee's colleagues tell her he is envious of her new responsibilities she tries to keep the peace in the office. Meanwhile, when Mona begins to see a therapist she realizes she has to take control of her life.

In an effort to make up her mind once and for all, Mona decides she wants to date both Chase and Lorenzo. When both men agree she finds herself more confused than ever. Dee Dee meets a new guy but when Brett tells her the relationship won't stand a chance, she sets out to prove him wrong. Meanwhile, Spencer meets a new woman and when she invites a friend to join them on the date he thinks his dreams have come true.