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.
Mona and Spencer are at odds about Delicious signing a heiress that can't sing. Spencer decides to go behind Mona's back to get it approved.
Mona decides to have a birthday party with Dee Dee, however Phyllis's gift ruins the event. Dee Dee ignores a job offer at law firm as a new opportunity appears.
Dee Dee clashes with her new co-worker and is upset when she has to work with him to get a new client.
Taking advantage of Dee Dee's grease fire, that brings a fireman to the building. Phyllis tries to set him up with Mona. However he's more interested in her.
Dee Dee and Brett run into problems with their client, a talented pitcher who won't sign his new contract because he wants to devote more time to his musical aspirations. Dee Dee asks Mona to listen to the man sing and dash his dreams of music stardom; but Delicious winds up wanting to sign him, leading to a rift between the sisters. Meanwhile, Big Dee Dee must break some bad news to Phyllis after Coco chases one of Phyllis's cats into traffic.
Mona goes against her initial instincts and decides to attend her ten-year high school reunion, where her professional accomplishments cannot protect her from the cruel comments of a pair of former cheerleaders. She perks up after a successful classmate takes an interest in her. Meanwhile, things do not go as planned for Spencer when he meets his on-line sweetheart in person; and Adam tries to get rich by stealing company supplies and selling them on the Internet.
When Spencer has trouble breaking-up with his new high-class girlfriend Gabrielle, he enlists Dee Dee to help break the bad news.
Meanwhile, Phyllis' boyfriend Glen plans a romantic get-away weekend, and she turns to an unlikely source for advice on her sex life.
Dee Dee uses a girl's weekend at the spa to set Mona up on a date. Spencer spends the weekend with Adam and his gay friends.
Charles and Spencer confront Brett about his sexist attitude towards Dee Dee.
Big Dee Dee throws herself a big party to make herslef feel better, however Dee Dee can't get the guest her mother wants. Mona feels that Chase is only about sex.
While throwing a baby shower for her ex-boyfriend and his new wife, Dee Dee notices that everyone is paired up except for her, and begins to struggle with her non-existent personal life.
Meanwhile, Mona begins to worry that her lack of maternal instincts will change how Chase.
Dee Dee is thrilled when she is asked to be a guest on a sports talk show hosted by Rodney Peete, and Mona tries to get a pampered singer to shoot a music video.
Mona makes plans to spend a romantic Valentine's Day with Chase, but she doesn't consult him about it. Adam gets annoyed with Franco, but he doesn't know how to tell him the truth.
After finding out that her rival, Naomi Dawson is giving Spencer the cold shoulder, Mona immediately confronts her, and Naomi reveals to Spencer that she is HIV positive.
Meanwhile, after being told to fire a difficult client, tennis player Melba Barnes, Dee Dee doesn't have the heart to follow through and attempts to give her a makeover to help her land a sponsor.
After being unceremoniously dumped by her wannabe-actor boyfriend on a reality TV show, Dee Dee is saddled with the unfortunate nickname, Desperate Dee Dee; so to show the world she is not desperate, she forces her way back onto the show, which proves to be an even bigger disaster.
Meanwhile, when Spencer reacts in a supportive and loving way after Naomi reveals she is HIV-positive, Naomi reevaluates her attitude and approach towards relationships, both present – and past.
Mona is in a sticky situation as Lorenzo goes to work for Chase, who knows about thier past together.
After discovering Brett will write her six-month job-performance review, Dee Dee invites him to dinner to butter him up, but things don't go as planned after they both have too much to drink.
Meanwhile, Adam guts his job after Mona and Spencer trick him into thinking he won a sweepstakes.
Despite Mona's commitment to her boyfriend Chase, a brief encounter with her ex-boyfriend Lorenzo leads her to fantasize about him and other men.
Meanwhile, after agreeing to financially support Adam's stand-up comic show, Big Dee Dee takes on a producer role, only to make the production all about her.
When Mona starts to take her break-up with Chase out on everyone by becoming rude and easily agitated, she puts her career in jeopardy.
Meanwhile, Dee Dee is caught in a moral dilemma on whether or not to continue a business relationship, when she believes her new married client Dwight Mitchell is having an affair; and Phyllis and Big Dee Dee suspect their daughters are planning a big surprise for Mother's Day, since neither has suggested plans to celebrate.
Mona decides to go to a therapist to cope with the breakup and discovers Chase is secretly spending time with her mom and friends behind her back.
Meanwhile, when Brett is left in charge of the office, Dee Dee tries to talk some sense into him to prevent the staff from hating him.
After deciding to take charge of her life, Mona decides to date both Chase and Lorenzo, who both agree, but later ask her to make a final decision.
Meanwhile, Dee Dee starts to date a health fanatic, but when Brett tells her the relationship won't work, she sets out to prove him wrong.