Toni suffers a breakdown after Greg cheats on her, then reveals that he only took her back so that he could get revenge against her. Lynn and Maya try to help her pick up the pieces, but Joan is less than sympathetic. Without Toni to round up male guests, William finds himself as the only man at Joan's Halloween party, and becomes overwhelmed by all of the female attention.

On the eve of their wedding, Yvonne learns that William hasn't told his mother about their relationship.

Joan decides to waive her ""three-month"" rule and sleep with Chris, but then receives a phone call from Sean. When she learns that Sean is back in town, she dumps Chris and expects to reunite with Sean. However, he stuns her by revealing that he is engaged. William expresses an interest in Lynn's co-worker, only to find that she is a lesbian with a crush on Lynn. Maya considers telling Darnell about her affair with Stan, but her friends talk her out of it. He soon discovers the truth in an unexpected way.

Joan forgives Toni for slapping her in Jamaica and trying to seduce Sean, much to the shock and dismay of Maya and Lynn (who has returned from Jamaica). When Joan's hair begins to fall out due to stress, she sees a therapist, who recommends that she cut Toni out of her life for good. However, this proves difficult when Toni seeks Joan's shoulder to lean on after a setback at work. Meanwhile, Darnell is upset by Maya's bixini wax, and accuses her of changing as the result of her association with the girls.

After an uncomfortable kiss, Maya realizes that she was wrong to get involved with Stan, and wants to stop seeing him. Stan, however, reveals that he has fallen head over heels, and refuses to give up on her. He seeks revenge by forming a friendship with Darnell and threatening to tell him about the affair. Meanwhile, William recuperates at Joan's house after being dumped by Yvonne.

Lynn's sister Tanya comes to town to help celebrate the anniversary of Lynn's adoption. Tanya, who is white, has immersed herself in African-American culture. Maya quickly befriends Tanya, but Joan and Toni grow annoyed with her for acting ""too black"" and get into a confrontation with her. Maya and Lynn defend her, but Tanya later takes things too far at the salon. Meanwhile, Joan tries to organize William's bachelor party.

After learning that Toni has shared details of her private life (her break-up with Sean and his sex addiction) with her boss, Mr. Swedelson, a fed-up Joan ends their friendship. Toni, who has just been fired, continually pleads with her to re-consider. Meanwhile, Vosco frustrates Lynn by refusing to get a job.

Maya befriends Stan, a man she meets at the office and helps get a job. He encourages her aspirations to return to school. Maya initially tries to fix up Joan and Stan, but soon grows jealous. Toni joins a protest against a rapper in the hopes of winning God's approval. William searches desperately for a best man.

Toni opens her real estate office and hires Lynn as her temporary assistant. However, Lynn quits after Toni proves to be too demanding a taskmaster. Toni quickly finds a very efficient replacement, but she also leaves when Toni won't let her have everything her own way. With her grand opening just days away, Toni becomes desperate to find someone to help her out. Meanwhile, Joan fears dire consequences from her boss after a judge throws out an important motion for a seemingly insignificant reason.

Toni plans to open her own real estate office, but Joan's efforts to encourage her to be practical wind up putting a damper on her enthusiasm. Toni accuses Joan of failing to support her dreams, although Joan insists that she just doesn't want her friend to get hurt. Meanwhile, Swedelson, disappointed by William's recent performance at work, encourages him to remedy what ails him by going on a ""booty call.""

Lynn moves in with William, and soon suggests that they take their minds off their recent break-ups by becoming ""sex buddies."" Joan is adamantly opposed to this, and warns that it will soon blow up in their faces. Shelby recommends that Toni adopt a more ""honest"" hairstyle to try to improve her business. Maya has difficulty finding child care for Jabari in the aftermath of her mother's move.

Stan gives Maya an expensive watch for Christmas. Joan tells her to give it back to him, but she refuses. When Darnell sees the watch, Maya claims it is a gift from Joan, leaving him infuriated. Meanwhile, Vosco finally packs up and leaves for good after Lynn criticizes his Christmas present to her--a dog. William is excited about playing Santa for the office Christmas party, but experiences unexpected problems after getting a stain on the suit.

Maya is stunned to learn that her mother has decided to sell her house and move away with her boyfriend. Toni's mother surprises her by coming to town for Joan's Mother's Day brunch. William eagerly anticipates a visit from his mother, who comes bearing a cake from his aunt's award-winning recipe.

Joan takes shots from her friends and is labelled a ""sell-out"" by the black community after she and William represent a beverage company suing a basketball star for accusing it of racism. Joan faces a larger moral dilemma after uncovering disturbing information about her client. Meanwhile, Lynn reluctantly takes a waitress job and moves with Vosco into a garage apartment managed by Maya's mother.

Joan lies to Dr. Bales about ending her relationship with Toni, but he runs into them having lunch together. Toni is furious to learn that Joan has been talking to a therapist about her, and orders Joan to end their sessions. Joan continues to keep her appointments, and Dr. Bales suggests that she be more assertive with her friends. Lynn's boyfriend, Vosco, arrives from Jamaica, and Lynn hides him in Joan's house. William suddenly becomes more attractive to women after becoming engaged. Maya is upset by his insistence on flirting with all of his new admirers.

On her 30th birthday, Joan grows depressed at the realization that she hasn't had a lot of excitement in her life. She determines that she will live life to its fullest in her thirties, and demonstrates her new philosophy by taking her friends to a nude beach--where they run into her father. Meanwhile, William suggests a pre-nuptial agreement to Yvonne, and is surprised by her response.

Yvonne accuses William of trying to control her after he surprises her by buying a house for the two of them. Joan objects to the firm's policy regarding Martin Luther King Day, as they insist on remaining open for the day. She goes out of her way to try to change Swedelson's mind about the topic. Maya continues to spend time with Stan, and William warns her about what he sees as Stan's true intentions.

Joan engages in surprisingly risky behavior after she begins dating a younger man, Chris. However, her friends urge her to re-consider the relationship after she inadvertently takes ecstasy at a night club. Meanwhile, Toni hires William as her attorney and tries to monopolize all of his time with trivial matters.

Yvonne panics when William seems hesitant to set a wedding date, as she fears that he is getting cold feet. A very reluctant Joan finds herself caught in the middle of the couple's relationship problems. After a chance meeting at a restaurant, Toni declares her love for Greg and manages to win him back. Lynn and Maya try to arrange a friendship between Darnell and Vosco in the hopes that their good qualities will rub off on each other.

Joan hooks up with a famous actor at the bar, but her friends tease her about the fact that he will only give her his pager number. Joan manages to pry his home number from him, but panics when he doesn't immediately call her back, and makes the mistake of repeatedly calling his number to let her friends hear his answering machine message. Meanwhile, Toni begins dating a single father and grows surprisingly attached to his young daughter. Maya uses her friends as a cover so that she can spend time with her ""friend"" Stan. Lynn tries to avoid Vosco.

Joan is the subject of office gossip and jokes after she begins dating a younger man who works in the mail room. She is embarrassed by the attention, and winds up hurting Chris's feelings. William is upset when Chris usurps his spot as pitcher on the company softball team. Maya fears that the persistent Stan will expose their involvement to Darnell.

Darnell is upset with Maya for buying an expensive dress at her friends' behest, and again when she returns it. He sees this as a sign that she doesn't trust him to provide for her financially. Sean has difficulty battling his sex addiction. Joan tries to help him out over the phone, and ultimately flies to New York to see him. He says that having sex only a few times a month is too difficult for him in his condition, and asks her to move to New York. Joan cannot do this, so they break up. Yvonne finally placates William by quitting the police force.