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.

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.

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.

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.

Dee Dee has difficulty preparing her law school valedictory speech because she is uneasy about the fact that she doesn't have a post-graduation job lined up. Big Dee Dee worsens the situation when she suggests that she give up on her career and just look for a man, then tricks her into going on a blind date. Meanwhile, Mona tries desperately to prevent her mother from moving into her neighborhood.

Mona and Dee Dee attend Neil's wedding, where their conversation with the already-nervous bride in the bathroom leads her to call off the wedding. Mona believes they should stay out of the situation to avoid causing further harm; but Dee Dee insists on taking in the devastated Neil when he shows up on her doorstep. Spencer regrets giving an overly generous tip to the stripper at Neil's bachelor party, and tries to get the woman to return it. Meanwhile, Big Dee Dee fears that she and Phyllis may actually have things in common after they run into each other at a funeral and discover that they both dated the deceased.

Mona grows very nervous about her role in selecting the Fast Track winner, especially after Kai decides to step aside and leave the decision about whom Delicious will sign to Mona. Dee Dee urges Mona to have confidence in her abilities. After a workshop, studio session and live showcase, Mona, Jimmy Jam and Terry Lewis select the winning act.

Mona tries to comfort Dee Dee after Carter appears on a talk show and says that he is seeing someone. When she later discovers that Dee Dee and Carter have secretly reunited, an angry Mona declares that she will not help Dee Dee pick up the pieces after the new ""casual"" relationship fails. Meanwhile, Spencer tries to get into photography in the hopes of getting rich; and Dee Dee and Big Dee Dee face a crisis involving their hair stylist.

In the hopes of getting closer to Phyllis, Dee Dee sets her up with her bitter divorced professor. However, the relationship soon fizzles, and the professor seeks revenge against Phyllis by turning her in for having too many cats. Phyllis blames Dee Dee, whose efforts to correct the situation only wind up making it worse.

Mona must work long hours as she prepares a major presentation for Kai about her talent search idea. She begins to lose touch with her family and friends, as she misses out on Dee Dee's weekly parties and is unaware of major news like Spencer getting a new girlfriend and Phyllis and Ray deciding to live together. Mona makes an effort to better balance her personal and professional lives, with disastrous results. Meanwhile, Adam, upset that being gay is no longer the ""in"" thing, decides that he is going to be straight.

Mona entertains overtures from the head of a rival record company, who hopes to hire her away from Delicious. She seeks her father's advice on how to handle the situation, leading to resentment from Phyllis. Meanwhile, Big Dee Dee plans a lavish 15-month ""birthday"" party for Drew in the hopes of showing up her friends.

After Ray says that he cannot make the Thornes' Thanksgiving dinner due to work commitments, Spencer invites his mother (who is unaware of his reunion with Ray) to fly in for the holiday. However, Ray arrives at the gathering unexpectedly. Spencer's mother constantly argues with Ray and lashes out at Spencer for keeping secrets from her. Phyllis and Ray decide to break up because he still has some lingering feelings for his ex. Meanwhile, Dee Dee pushes Mona to be more honest with their father about her frustration over his limited involvement in her life.

Mona becomes upset when Kai repeatedly refuses to give her credit for the Fast Track contest in interviews. Mona, at her family's urging, tries to seize some of the credit for herself, with disastrous results. Meanwhile, Big Dee Dee gets in touch with her agent so that she can resume her acting career. She winds up playing second fiddle to Coco in a dog food commercial.

Phyllis recruits Mona, Spencer and Adam to help out with a telethon on Mother's Day. Big Dee Dee and Dee Dee also decide to participate. Phyllis grows so frustrated with Big Dee Dee's interference at a pre-telethon meeting that she blurts out that Big Dee Dee was pregnant before she got married. Dee Dee is shocked and hurt by the fact that this was kept a secret from her, while Mona gives Phyllis the silent treatment because she is fed up with her bluntness and inability to keep her mouth shut.

After Dee Dee learns that her mother's co-star in a new play is engaged to Dee Dee's idol, esteemed attorney Maxine Shaw, Dee Dee sees an opportunity to atone for a bad interview she once had with the woman. However, Dee Dee believes she has lost her chance after Big Dee Dee (who had to finance the play to ensure she could star in it) gets Max's beau fired because she fears he will take attention away from her. Meanwhile, Mona must find a way to rein in her co-workers after Kai is delayed and leaves her in charge of a company retreat at a resort.

Mona returns from a Hawaiian vacation and clears the air with Spencer. They reaffirm their decision to just be friends. While looking through some vacation photos with her family, Mona reveals that she can now ride a horse. She is stunned to learn that Dee Dee still has the horse their father gave her as a child, Daddy's Favorite, and that she has lied for years about having not kept the horse. (The horse led to a major rift between Charles and Phyllis that separated the sisters for a decade.) Mona decides to buy her own horse, but it doesn't quite go as planned. Meanwhile, Adam helps Spencer uncover the cause of Kai's sudden unpleasant attitude toward him.

Mona pretends that Drew is her son in the hopes of winning over an artist that she is trying to sign who is a single mother. After her plan fails miserably, she suggests that Delicious stop chasing after artists that they have no chance of signing and instead conduct a talent search. Spencer continually bad-mouths all of Mona's ideas, and the two snipe at each other. Adam advises Spencer to finally deal with the tension between Mona and him before it destroys their friendship. Meanwhile, Dee Dee obsesses over trying to build a cabinet without any assistance; and Big Dee Dee drives Charles crazy when she tries to get over her depression by scheduling lots of ""quality time"" for them as a couple.

Dee Dee is furious to discover that Mona has become friends with Dee Dee's rival, Stephanie Seymour, after meeting her through a work event. Dee Dee insists that Mona should dislike the same people that she does because it is her duty as a sister. Mona tricks the duo into having tea with her in the hopes of getting them to make peace, but things do not exactly go the way she had planned. Meanwhile, a rejected applicant for the talent search refuses to take no for an answer.

Mona panics when a screw-up by Spencer may cost Delicious a chance to have mega-successful producers Jimmy Jam and Terry Lewis help judge a showcase with the talent search finalists. Meanwhile, Dee Dee tries to prove to Mona that she can get by without their father's assistance after she gets downsized from her new job before her first day.

Mona and Dee Dee agree to get each other dates as a birthday present. Dee Dee does some thorough research and finds Mona a seemingly perfect guy, James, and the two get along well enough to set up a second date. Mona waits until the last minute to begin her search and is forced to turn to a less-than-helpful Spencer and Adam as she tries desperately to track down someone for her sister. Meanwhile, Dee Dee convinces a reluctant Big Dee Dee to let Mona and Phyllis join them for a mother/daughter portrait sitting. Big Dee Dee and Phyllis see the photograph as another opportunity to outdo each other and go all out to find the flashiest outfits possible.