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 refuses to go along with Spencer's desire to sign a talentless but popular heiress to Delicious. He infuriates her by finding a way to pitch his proposal without her approval. Meanwhile, Big Dee Dee is jealous when Phyllis teaches Dee Dee a series of money-saving tips to help her adjust to her new financial standing.

Mona decides to embrace her birthday for a change and throw a party honoring Dee Dee and her. However, the event is spoiled by Phylllis's gift to Mona: a certificate to have her eggs frozen at a fertility clinic. Meanwhile, Dee Dee receives a great job offer with a law firm, but decides to pass because her instincts tell her something else will come along. Her friendship with an NBA star soon leads to a new opportunity for a career.

Dee Dee begins work as a sports agent, but clashes with a cocky co-worker. They are both upset when their boss forces them to work together to bring in a hot football player. Meanwhile, Adam recommends that Mona and Spencer follow his lead by signing up for an online dating service. They decide to write each other's profiles after having difficulty completing them on their own.

After Dee Dee starts a grease fire in her apartment, a handsome fireman rescues one of Phyllis's cats from the building. Phyllis eagerly tries to set him up with Mona, but the man winds up being attracted to Phyllis. Meanwhile, Adam falls into a funk over his friends' successes, especially after learning that Spencer has purchased his own home. Spencer tries to cheer Adam and convince him to set some goals for himself.

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.

Spencer seeks Dee Dee's advice to land a sophisticated woman, and again turns to Dee Dee for help ridding himself of the woman when she proves to be unbearably controlling. Gabrielle repeatedly refuses Spencer's efforts to break up with her. Meanwhile, Mona reluctantly gives Phyllis some advice before her first big romantic weekend with Glen. Dee Dee plans a bachelor party for a client.

Dee Dee tricks Mona into joining her at a singles weekend at an exclusive new hotel. Mona meets a handsome bartender, but Dee Dee repeatedly tries to steer her away from him, claiming that she has her best interests in mind. Spencer and Adam also attend the event, thanks to Adam's successful friend. Spencer enjoys the perks of hanging out with Adam and his friends, but is surprised to discover that people believe he is also gay. Meanwhile, Big Dee Dee convinces Phyllis that her presence in the building and relationship with Glen are driving Mona away.

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 realizes that she needs to slow down her relationship with Chase after they start spending so much time having sex that it begins to affect her job and other aspects of her life. Dee Dee plans a "legends ball" on behalf of her mother (who is depressed because of her floundering acting career), but finds that none of the invited guests want to attend. Spencer buys a gigantic new truck that soon leaves him financially strapped because he can't afford gas.

After throwing together a baby shower for Neil and Janet, Dee Dee becomes concerned by the fact that she is the only person in attendance who is not attached. She begins to question her life and decision to pursue her career so aggressively. Meanwhile, Mona worries that her lack of maternal instinct could have a negative effect on her relationship with Chase. She tries spending time with Drew, and receives some advice from Big Dee Dee.

Dee Dee receives the opportunity to appear on a sports talk show, only to humiliate herself by falling flat on her face. Mona objects when Spencer and Adam constantly give in to Dalis's petty demands. She finally puts her foot down, with disastrous results.

Mona fears that Chase hasn't made any special plans for Valentine's Day, so she tries to take action. Dee Dee sets Brett up on a blind date in the hopes of curing him of his bad mood concerning the holiday, which stems from a broken engagement. Spencer gets close with a rival music executive whom Mona despises. Adam grows irritated with his Valentine's date, a man with whom he's shared a yearly tryst for the past 10 years.

Mona continues to bristle at Spencer's relationship with Naomi, who seems strangely reluctant to become romantically involved with him. Mona's mother and friends encourage her to put her personal feelings about Naomi aside and help Spencer. Naomi later divulges a surprising secret to Spencer. Dee Dee has difficulty following her boss' edict to drop a female tennis player with limited marketability. Big Dee Dee gets a potential break in her acting career when she's given a callback for a low-budget horror movie.

Spencer continues to shower Naomi with affection after she reveals her HIV-positive status. However, her newfound confidence prompts her to dump him and seek to profess her love for another man. Mona tries to comfort Spencer, but he rejects her for failing to back him throughout the relationship. Dee Dee agrees to join her new actor boyfriend in a reality show, and winds up humiliated. Charles is surprisingly supportive when Big Dee Dee is asked to do a nude scene in her film debut.

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.

After finding out her rival will be writing her six-month performance review for the agency, Dee Dee makes an effort to tighten up her relationship with Brett outside the office. The two have a little too much to drink one night and wake up the next morning in Dee Dee's apartment clueless as to how they got there. Mona and Spencer trick Adam into thinking he won a sweepstakes.

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 is taking her break-up with Chase out on everyone, only to realize that she's also putting her professional career in jeopardy. Dee Dee's newly signed client is married but when she suspects he's having an affair she is faced with a moral dilemma. Meanwhile, Phyllis and Big Dee Dee assume the girls are planning a big Mother's Day celebration, since neither has suggested plans to celebrate.

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.