Joan Clayton, a successful attorney, prepares to celebrate her 29th birthday (although she claims to be 26 to make her achievements seem more impressive). 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. Toni tries to hide the truth, but their friend Lynn forces her to confess to Joan. 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. Joan is furious to learn that Charles is now interested in settling down, and the evening comes to a screeching halt. Meanwhile, Toni constantly clashes with Maya, Joan's sassy assistant.

After Joan reveals that she hasn't had sex in a year, her friends push her to go for a one-night stand. Joan is reluctant because she generally doesn't sleep with anyone until she has been in a relationship for three months, but tries to make a move on Davis Hamilton, a handsome man who owns the restaurant the girls frequent. She convinces Davis to drive her home and makes a pass at him, only to learn that he is engaged. Although nothing happens between them, Joan tells Toni and Lynn that she slept with him. When the girls blab the news around town, Davis' fiancée dumps him, leaving Joan to struggle for a way to clean up the mess.

Joan, Toni and Lynn set up dates with men they met over the Internet. Lynn's guy never shows up (his parole was denied), while Toni rejects hers because his skin is too dark. Although conspiracy theorist Maya warns that he will turn out to be a serial killer, Joan is pleased with her date, Marcus. 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. Meanwhile, William also uses the Internet in an attempt to find love. He finally gets a date, but the woman seems to be completely crazy.

Joan grows tired of the clingy Marcus and plans to break up with him, but only winds up complicating the situation by having ""pity sex"" with him. The girls try to help her out by bombarding Marcus with negative facts about Joan in the hopes that he will dump her. Meanwhile, Maya gets involved in a get-rich-quick scheme.

Joan plans an elaborate scheme to get revenge on William for the latest in a series of Halloween pranks. Toni is put off when her date asks her to engage in a threesome--with a stuffed animal.

Joan finds herself alone on Thanksgiving after everyone makes other plans for the holiday. After dining at 847, she meets Davis's friend Preston Hall, a handsome and highly successful attorney. Joan invites him back to her place for a home-cooked meal before he has to leave on the red-eye, but her friends suddenly begin appearing and she can't seem to get them to leave.

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.

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.

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.

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 meets her biological mother, Sandy, who suddenly appears at Joan's house. Although the two initially become friends, Lynn soon becomes embarrassed by some of Sandy's behavior. However, Lynn becomes intrigued by a documentary project about sexuality, and quits her job to help her work on it. Meanwhile, Joan and Maya drive each other crazy as Maya and Jabari stay with Joan while Maya looks for an affordable apartment.

Toni realizes she has fallen for Todd after he protects her during an altercation with a man on the street, but is still reluctant to date him because of his size. Joan is appalled when Ellis rates her only a 5.5 on looks on a scale of one to ten.

Lynn persuades Toni to accompany her to Virginia, where she seeks Sandy's help before a presentation aimed at receiving a grant for her AIDS documentary. During the visit, Lynn meets her grandmother and learns a shocking secret about Sandy's health. After discovering how much money William is now earning, Maya tries to become his assistant in the hopes of improving her salary and returning to school. However, William will only sign off on the arrangement if Joan gives her approval.

Joan enjoys relative peace in her relationship with Ellis. However, she establishes a strong connection with a stranger whom she meets when they duck into the same doorway during a rainstorm. She is later surprised to find that the man is Ellis's agent, Brock. Brock meets with Joan outside a play when Ellis is called away to a meeting. They begin kissing, and end up back at Brock's place, where they declare their love for each other. Brock feels it is wrong to sleep together while she is still Ellis's girlfriend, so Joan promises to break things off. However, Ellis surprises her by finally telling her that he loves her. Sivad pressures Lynn to move out of William's house. He initially doesn't want to live with Lynn, but soon changes his mind. Toni grows annoyed with all of Todd's habits. After he reveals that he is deep in debt, she leaves him and shows up at Joan's house. William continually tries to get Maya to actually do her job, but she spends all of her time reading se

Toni refuses to speak to Todd because she is up in arms about his debt and feels betrayed by the fact that he failed to disclose this information sooner. While at the spa with Joan, Toni's ring is apparently repossessed by a woman on behalf of Harry Winston. A furious Toni plans to divorce Todd, but seems to soften as she discusses the situation with William. However, she still tries to throw Todd out of the house. After she explains that her greatest fear is becoming poor again, Todd says that he is afraid of losing her, and points out that he accumulated his debt trying to court her. Toni learns that Todd did not buy her ring at Harry Winston; the woman simply stole it after overhearing her conversation about debt. Todd gets Toni to agree to work on the marriage, and they reach a compromise about the insurance settlement for the stolen ring. Meanwhile, Joan confides in her new assistant, Peaches. She says that Ellis is away in New Zealand working on his movie, but she has dec

With her bills piling up, Maya is forced to consider a job writing for a porn publisher (which already employs Lynn). She turns down the position due to moral objections and resumes selling her book on the street. When she has little success--due in part to bootleg sales--Maya decides to give up on her dream and go back to working as a legal secretary. This does not work out, and she winds up accepting the job at the porn publisher. Fortunately, she is soon able to quit after her writing aspirations get a boost from a surprising source. Meanwhile, William and Joan quarrel after he goes home for Thanksgiving without her; and Toni vows to not talk too much about her pregnancy.

William surprises Joan with a romantic Christmas getaway in Puerto Rico, but they wind up stuck at a seedy motel after a blizzard strands them in Cincinnati during a layover. Meanwhile, Lynn, Maya and Toni take advantage of Joan's absence to enjoy the holiday at her house without all of her strict Christmas rules and other demanding behavior.