Dee Dee assigns herself the task of personally helping Mona get over her break-up with Nick. She spends nearly every minute with her and forces her to attend an exercise class. Spencer and Mona plan to go away on a road trip, but Dee Dee forbids this because she is afraid of what might happen. While having lunch, Mona and Dee Dee run into Phyllis and her boyfriend, Ray. He is a popular local disc jockey whom she met after calling in a traffic tip. Dee Dee invites them to a dinner her parents are organizing in honor of her new internship. Mona finally ditches Dee Dee and goes to see Spencer. They discuss the fact that they are doing well after their break-ups, and how lucky they are to have each other. They begin kissing passionately, but Mona quickly leaves. Dee Dee is horrified, but Mona says that it felt right. Spencer confesses what happened to Adam, who warns him that Mona is still fragile but thinks they would be good together. At Dee Dee's dinner, Phyllis announces tha

For Mother's Day weekend, Big Dee Dee and Dee Dee vacation at an exclusive spa. Not to be outdone, Phyllis and Mona do the same, and end up in the room next door. The weekend quickly goes from weird to worse when Dee Dee blurts out that she wishes her mom was more like Phyllis.

Spencer's cousin Chauncey begins working in the mail room at the record company and blabbing everyone's secrets. He recalls the time in college that he walked in on Spencer and Mona apparently in the midst of a drunken tryst, creating friction between Spencer and Camille. The story prompts Mona to confront her feelings for Spencer, as she wonders if the reason she has been so jealous of his girlfriends is because she wants him for herself. Meanwhile, Dee Dee creates a mold of her mother's pregnant belly--which Big Dee Dee hates.

Mona fears that her new man is too good to be true, so she searches for his hidden major flaw. Dee Dee accuses her of being paranoid, but soon discovers that Mona has reason to be wary, as Roland is living out of his car. Big Dee Dee considers having her breasts enlarged, but winds up receiving comfort from Phyllis as she faces a potential health crisis. A bored and desperate Dee Dee puts on a show for an apparent peeping tom in the building across the street from her apartment.

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.

When Mona mistakes a dinner date with a handsome reporter as a personal affair, she unwittingly gets quoted in a music magazine saying disparaging things about one of her music label's artists that ends up getting her fired. Meanwhile, Dee Dee utilizes her law school knowledge to try to get the story retracted.

Camille returns from a vacation in London and behaves coldly toward Spencer. She finally admits that she is desperately homesick and has decided to move back to England. Phyllis upsets Mona by giving her a gift, a cat she saved from a shelter. (She sees it as a sign that Phyllis has given up on Mona ever giving her grandchildren.) Big Dee Dee decides to record a song as a birth announcement. Mona helps Dee Dee and Big Dee Dee search for an affordable studio. Mona meets Nick, the charming and handsome producer who runs one of the studios. They immediately hit it off and make a date. She has to cancel to tend to Spencer, but Nick is understanding, and later shows up with food. Dee Dee counsels Spencer and encourages him to tell Camille his feelings. He is devastated to find that she was about to leave without saying goodbye. She says that she enjoyed their relationship, but that it moved too quickly for her. Mona doesn't have enough time to look after the cat, so she gives it

When Dee Dee becomes frustrated with Neil because he does not seem interested in getting intimate, he divulges that he is celibate. Meanwhile, Mona is under pressure at work and takes up smoking again, but she is too embarrassed to admit it and tries to hide it from her family.

After Mona complains about being bombarded with demos and Spencer's refusal to pay back his debts, Dee Dee encourages her to become more assertive and not let people take advantage of her. Mona follows her advice and re-possesses Spencer's new jacket and shoes. However, Dee Dee's words come back to haunt her when her sister refuses to listen to a demo by Dee Dee's handsome and influential new boyfriend. Meanwhile, Phyllis enjoys being pampered at an expensive shoe store after a salesgirl mistakes her for Big Dee Dee.

Mona fears a lonely Valentine's Day, but her tears may be for naught when two men from her (recent) past both ask her on dates. Also, Dee Dee is miffed that Neil would choose work over her. Meanwhile, Big Dee Dee is angry with her husband, who also chooses work over her.

Mona tells her friends and family that she doesn't want to celebrate her birthday, as she would rather spend the day alone in quiet reflection. However, she soon becomes extremely bored. She is relieved when Big Dee Dee shows up, although she has actually forgotten Mona's birthday and is just there to see Dee Dee. The two go down to the laundry room in pursuit of Big Dee Dee's dog, and wind up trapped when an earthquake hits. They share a picnic lunch and have a revealing talk about their relationship. Meanwhile, Phyllis tracks down Charles to try to convince him to help buy a car for Mona's birthday, and they wind up stuck in an elevator. The earthquake also traps Dee Dee, Adam and Spencer in an upscale store as they shop for Mona's gift. Everyone is embarrassed when Spencer has a panic attack after the earthquake.

Phyllis announces that she has been seeing someone for the past month. She reluctantly agrees to bring her boyfriend, Earl, to the apartment to meet the girls. Earl is handsome, sweet and romantic, and leaves everyone (including Big Dee Dee) sufficiently impressed. Dee Dee sees Earl at a restaurant with another woman, and learns that it is his wife. Mona and Dee Dee try to break the news to Phyllis, and are stunned to discover that she already knew that Earl is married. She believes that he is separated and about to get a divorce. Mona and Dee Dee try to convince her to stop seeing him. Meanwhile, Spencer discovers that being attached has suddenly made him virtually irresistible to other women.

After hiding the relationship for a month, Dee Dee reluctantly introduces Carter to her parents. They are surpisingly supportive. However, Big Dee Dee immediately goes to Mona and pleads with her to try to sabotage the relationship, as she and Charles believe that Carter is completely wrong for Dee Dee. Dee Dee is furious, and winds up surprised by Carter's reaction to the situation. Meanwhile, Kai provides Mona and Spencer with an assistant, who livens up the office but doesn't seem to do any actual work.

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.

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.

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.

After another failed relationship, Mona decides to focus on her career for a while. She is determined to help Zora, a promising young singer, secure a contract with the record company. Zora mistakes Mona's efforts to boost her confidence for romantic interest and develops feelings for her. She confesses her crush to Adam, who keeps the news to himself so that he can watch the sparks fly. Mona struggles to come up with a way to handle the situation without hurting Zora's feelings. Meanwhile, Dee Dee dates a man who pays way too much attention to her feet.

Dee Dee organizes a singles mixer at a local club. She bristles at Mona's claim that she only dates a certain type of man (well-groomed and upwardly mobile), and tries to prove her wrong by picking up a tough guy named Keno. She takes off with him on his motorcycle and joins him at a bar, where she rides a mechanical bull. She has a good time exploring this new side of herself--until she runs into a very angry woman who claims to be Keno's girlfriend. Mona and Nick crash the mixer and meet up with his ex-girlfriend, Raquel. Mona is disturbed to discover that Raquel is her dead ringer, and fears that Nick is just with her because of the resemblance. Meanwhile, Dee Dee must actually care for Drew herself after firing the nanny. She is mortified when she must turn to Phyllis for help when her son will not stop crying.

Big Dee Dee, Phyllis, Mona and Dee Dee make plans to spend Mother's Day together at a brunch/concert. Mona is surprised to learn that Dee Dee plans to get Phyllis a present. She scrambles to find something appropriate for Big Dee Dee. Big Dee Dee grows tired of receiving gifts meant for the baby and is thrilled with Mona's gift of Louis Vuitton luggage. This upsets both Dee Dee and Phyllis, who had already bristled at the fact that Mona was spending more time with Big Dee Dee. Phyllis starts complaining about her gift (even though it is the watch she repeatedly requested). Dee Dee suddenly gives Phyllis a diamond bracelet in an attempt at one-upmanship. At the brunch, Phyllis and Big Dee Dee discover that their gifts may not have been as thoughtful as it seemed. Everyone is at each other's throats, until the bathroom attendant, separated from her family for the day, forces the mothers to see the error of their ways. Meanwhile, Charles and Spencer watch Drew while the women are

Kai reluctantly agrees to give a shot to Spencer's friend RJ Jackson, a talented and successful singer with a reputation for partying. Spencer has difficulty reining in RJ, and must resort to desperate measures to get a track recorded before the deadline. Meanwhile, Big Dee Dee decides to return to the stage after helping Adam prepare for an acting showcase.

Dee Dee makes a date with her favorite author after meeting him at a book signing. All appears to be going well, but Dee Dee reconsiders the relationship after learning that Carter has full custody of his two young daughters. Meanwhile, Phyllis begins snapping at everyone and seeks refuge at Mona's apartment after disagreeing with Ray's decision to take on another shift at the radio station.

After Dee Dee bests her at an online word game, Mona grows frustrated by the fact that she always loses to her sister. She becomes determined to beat her at something, and sees her opportunity when Dee Dee organizes a poker party for one of her law school professors. Their mothers decide to crash the event, where Phyllis winds up winning Big Dee Dee's wedding ring in the pot. Meanwhile, Adam tries to get access to a copy of Spencer's personal music playlist.

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.

After Dee Dee loses her old room to the baby and Big Dee Dee misses several appointments, Dee Dee begins to worry that the baby is forcing her out of her parents' life. She suffers from so much stress that she has a breakdown and hears a doll talking to her. Mona recommends that she make an appointment with Phyllis to discuss her problem. She says that she feels as though she is the only one who is worried about the way the baby will change her life. Phyllis assures her that her reaction is perfectly natural and that she should air her concerns with Big Dee Dee. Before she gets around to it, Big Dee Dee admits to her own anxieties about the child's birth, and thanks Dee Dee for her support. The conversation reassures Dee Dee about her importance in her mother's life. Meanwhile, Spencer continually cancels on Mona because of plans with Camille. She looks to Adam to take his place, but Adam isn't too thrilled about this.

Camille sets up Mona on a date with her best friend, the handsome and engaging Carlo, whom she hasn't seen for years. Mona is thrilled when she and Carlo hit it off, and believes he might be a long-term boyfriend prospect. However, Carlo is actually in love with Camille and wants to pursue a relationship with her. Meanwhile, Dee Dee and Big Dee Dee are desperate to find out the sex of the baby, while Charles insists that they should wait until the birth. The women try to go behind his back to the doctor.