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.

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.

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.

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 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 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.

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.

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.

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 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.

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.

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.

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.

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.