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.

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.

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.

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.

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.

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.