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 h…

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 …

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…

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 …

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 i…

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 mu…

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 success…

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…

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 Ada…

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 encour…

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 (…

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…

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 di…

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 engagem…

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.…

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…

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,…

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…

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 an…

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 mo…

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 o…

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…