Kaplan October 14, 2002 2002-10-14 Joan has several run-ins with an actor at the gym, but finds herself attracted to him. She seeks her friends' advice on how to help Sean improve his performance. Donna is unnerved by the closeness between Joan and William, particularly when they take it upon themselves to help her organize a Cinco de Mayo party for the convalescent home where she works and get really excited about it. William is excited about playing Santa for the office Christmas party, but experiences unexpected problems after getting a stain on the suit. However, this proves difficult when Toni seeks Joan's shoulder to lean on after a setback at work. However, Ellis surprises her by finally telling her that he loves her.
However, he stuns her by revealing that he is engaged. Joan claims she has no problem with Toni bringing Charles to her birthday party; but then brings her friend and colleague, William, to try to make him jealous. Hicks September 26, 2005 2005-09-26 Maya and Darnell continue to bicker. Maya continues to spend time with Stan, and William warns her about what he sees as Stan's true intentions. 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.
However, when the girls show up at a party, Alex refuses to allow them to come inside. Joan is surprised to run into William, who has come to New York to give legal advice to Maya. Although her friends believe she is overreacting, Maya insists that Darnell wants her back and determines that she must make a move on him. Toni agrees to help Joan clean out her house, but insists that Joan's love life is what actually needs to be purged. Meanwhile, William worries that the fact that he and Donna have such different backgrounds she cleans bed pans for a living and insists on traveling by bus will impede their chances of having a future together. Hicks March 4, 2002 2002-03-04 Joan is the subject of office gossip and jokes after she begins dating a younger man who works in the mail room.
Meanwhile, Maya is annoyed with Darnell when she discovers he knew about William's doubts and didn't share the information with her. Ellis tries to make it up to her by doing a magazine interview with her. Meanwhile, William starts to regret his marriage proposal to Monica. She decides to buy him out to preserve their friendship, but he refuses to accept the check. While waiting for her chance to perform, Lynn falls asleep and misses her turn on stage. When Joan and Lynn pressure Maya for the real reason she is opposed to moving, Maya reveals that she is pregnant. She proceeds to annoy everyone with her original compositions.
Yvonne forces William to call his mother, but she refuses to give her blessing and theorizes that William never told her about Yvonne because he doesn't really want to marry her. Maya, with help from Toni, seeks medical attention after she and Darnell have difficulty conceiving a second child. William tries to win back the girls' trust following the Christmas Eve debacle. Joan freaks out after discovering that Marcus wears a girdle because he has large hips, prompting Toni who had taken heat from the girls over her treatment of her date to take her to task for her behavior. Maya gets upset and feels that Joan is trying to make her house the hang-out spot once again and Lynn gets caught in the middle. Joan's mother explains that she did not sleep with William; she had gone to his house to talk, and was in a robe because she needed to shower before her flight. She also resumes training for the Los Angeles Marathon just weeks before the event in an attempt to take her mind off Toni.
Meanwhile, Sivad feels threatened by Lynn's past with William and orders her to move out of William's house; and Mrs. Meanwhile, Joan is uncomfortable using the bathroom at Aaron's house because she wants to maintain a sense of mystery in their new relationship, and Monica and William seek out advice from Lynn on how to spice up their sex life. Meanwhile, William worries that he will lose one of his few male friends when the man begins dating Maya. Kaplan November 3, 2003 2003-11-03 William convinces Joan to host a baby shower for his sister, Linda; and her partner, Kira. Toni and Todd prepare for the custody battle, William runs into Monica and insist to rekindle the old flame, Maya learns of Darnell's offer to Florida to join a pit crew, and Joan's night ends as bad as the next day begins. Toni, Joan's best friend, begins dating Charles, a venture capitalist with a propensity for toe-sucking who dated Joan until he freaked out at the prospect of marriage.
Todd tells Toni that their marriage is over because she doesn't trust him or care about him. Meanwhile, Toni constantly clashes with Maya, Joan's assistant. Toni has great difficulty adjusting to motherhood, but pushes Todd away when he tries to help her. They find the counseling pointless, but engage in an afternoon tryst that has an overly enthusiastic Maya convinced that they are going to reunite soon. Joan tries desperately to get Toni to forgive her and allow her to be a bridesmaid. Joan grows fed up with her lack of support and tells her off, prompting Carol to leave.
Lynn decides to take the executive up on his offer, but is embarrassed the next day when he ignores her. Joan and William spend the night together, but discover that they are not physically compatible. They insist that he is actually upset about the break-up with Joan, and pressure him to share his feelings. Although the misunderstanding is cleared up, Joan begins to have second thoughts about William. Todd fears that Toni still has feelings for Greg and threatens to leave her if she sees him. Meanwhile, William orders Lynn to leave his house, but continually sabotages her efforts to find a roommate. Meanwhile, the mother of Lynn's ex-boyfriend Lenny goes all out to try to reunite him with Lynn.
Meanwhile, Joan and Maya drive each other crazy as Maya and Jabari stay with Joan while Maya looks for an affordable apartment. William searches desperately for a best man. When Joan confronts William about Monica's new position, he reveals that he has made a mistake proposing to Monica but can't tell her. Joan angrily breaks up with Frank in public. He promises to support her financially and let her live at his place. Meanwhile, William and Joan quarrel after he goes home for Thanksgiving without her; and Toni vows to not talk too much about her pregnancy. The two wind up commiserating about their romantic problems.