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 grows impatient with Sean, who refuses to kiss or touch her. After discussing a number of possible explanations with her friends, she finally pushes Sean for the reason behind his cold behavior. Joan is taken aback when he confesses to being a sex addict. Meanwhile, Toni annoys Greg with her refusal to make a commitment to him; and Yvonne angers William by sharing a few too many intimate details about their love life with Maya.

Toni remains in a state of despair over her split with Greg, while a guilt-ridden Joan continues to keep her involvement in the break-up a secret. She confesses to Greg, who still wants nothing to do with Toni. William worries when Yvonne heads off to Jamaica to attend Sinbad's music festival. The girls decide to go to Jamaica as well, as Joan hopes that Toni will meet someone and get out of her funk. Sean and Joan argue, as he feels she should either confess the truth or mind her own business. Maya gets her groove back after a bikini wax, and Lynn falls in love with a bellhop and decides to stay in Jamaica. William shows up and surprises Yvonne with a marriage proposal. Toni hits it off with NFL star Terrell Davis and accepts his proposal, although she admits that she still loves Greg. Joan finally confesses that she told Greg about Toni's engagement to Clay, prompting Toni to attack her and storm off. Joan returns home to find Sean and Toni in a compromising position.

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.

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.

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 fears she has hit an all-time low after she holds a ""Bring Your Ex"" party, but doesn't get a single phone number. She eventually winds up swearing off men to train for a marathon. Maya still struggles to get Darnell to talk to her after a month apart. William threatens to throw Lynn out of his house unless she lands another job. Toni laments the lack of drama in her life.

Ellis goes all out to give Joan a magical Valentine's Day, but the couple's future is put in jeopardy when he learns that his ex-girlfriend is about to have their child. Toni finds her Valentine's Day card from Todd offensive, and fears that he is only dating her because she is black. William cannot bring himself to tell Monica that he quit the law firm.

Joan promises to support Toni as the wedding approaches, but repeatedly neglects her in order to deal with her latest drama involving Ellis, who has failed to tell her that the mother of his child has been cast as his love interest in his movie. As a result, Toni tells Joan that she is not welcome at the wedding. Meanwhile, Sivad feels threatened by Lynn's past with William and orders her to move out of William's house; and Mrs. Childs fiercely tries to keep Maya away from Toni's med student brother, Antoine.

Joan tries desperately to get Toni to forgive her and allow her to be a bridesmaid. However, it remains to be seen if there will even be a wedding, as Todd walks out on Toni because of her selfishness. Meanwhile, Lynn objects to Sivad's decision to write a poem for the wedding.

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

After Brock invites Joan to join her for a weekend in Las Vegas, she is convinced that he plans to pop the question. She brags about this constantly to her friends, but isn't so sure that she is really ready for marriage. She drives Brock crazy as she constantly makes him turn back to Los Angeles and then toward Vegas again, and even after he says that he is anxious to marry her, she continues to battle cold feet. Meanwhile, William carries around a baby doll to try to prove to his sister that he can handle the responsibilities of caring for a child.

Maya self-publishes her book, Oh, Hell Yes, and sells it on the streets, where it is a tremendous success. Ronnie tells her that a major publisher wants to offer her a five-figure deal to release the book. Toni repeatedly tries to call Todd in New York, but he refuses to return her messages. She continues to act as though nothing is wrong in front of her friends, even when they express concern about her well-being. Lynn gets a new boyfriend, Lenny. Her friends note their physical resemblance and all the things they have in common (including allergies) and offer the opinion that they might be brother and sister. Lynn talks with Lenny's parents, who assure her that this is not the case. She breaks up with him because she is still freaked out at the idea that he could have been her brother, and decides to search for her birth father. William decides not to confess his feelings for Joan, and pursues an attractive woman he meets at the bar. However, he runs into Joan when she stops

Maya learns that the publisher wants to sanitize her book to make it more accessible to white readers. She convinces her editor to stand up for her vision and get the original version of the book released. She succeeds, and Maya receives $25,000. After William shows up at her house to confront her, Joan flees for New York with Toni. Toni sees Todd with his colleague, Natalie, and again assumes he is cheating on her. She makes a scene on the set as she begs him not to leave her. Joan is surprised to run into William, who has come to New York to give legal advice to Maya. Joan tries to tell William that she isn't interested in him romantically. He says that this is okay, and that things between them will soon return to normal. William runs into Monica, his evil, golddigging ex-girlfriend. Lynn visits her birth mother, Sandy, for information on her biological father. She learns that Sandy wanted to marry Lynn's father, but Sandy's parents paid the man to go away. They claim it

Joan tries to confess her feelings for William, but knocks on the wrong door and winds up on the run from a crazed lesbian who thinks that Joan stole her girlfriend. Joan is repeatedly thwarted in her efforts to try to share her feelings with William, and gives up after he ignores her to have a tryst with Monica in the airplane's bathroom. Lynn returns to her birth father's house and admits that she is his daughter. Todd refuses to believe that Toni is pregnant unless she takes another test. She refuses, and orders him to be on the plane back to Los Angeles the next day. When he does not show up, she tries to hold up the plane to make everyone wait for him.

Joan's mother makes a surprise visit and constantly criticizes her, particularly anything regarding her decision to open the restaurant. Joan grows fed up with her lack of support and tells her off, prompting Carol to leave. Joan also grows tired of fighting with William about the restaurant. She decides to buy him out to preserve their friendship, but he refuses to accept the check. They discuss his previous love confession, and William angers Joan by saying that he was ""desperate."" A ranting Joan winds up admitting that she tried to go to his New York hotel room to confess her feelings. They kiss and admit their love for each other, but Joan collapses when her mother emerges in a bathrobe. Meanwhile, Maya is concerned when she discovers that Jabari has been watching pay-per-view porn.

Following Darnell's drunken love declaration, Maya enlists the help of Joan and William as she plans to break up his wedding. However, she soon has second thoughts. Joan tries to talk some sense into Darnell in the bathroom. Meanwhile, Toni gives birth to a baby girl before she is able to get in touch with Todd or the girls. Following the surprisingly easy delivery, Toni begins to wonder whether she really needs Todd in her life. Unable to hold back her feelings any longer, Lynn lashes out at Finn and quits the band.

Maya remarries, Toni demands a divorce, Lynn gets engaged and Joan freaks out. After a passionate reunion, Maya asks Darnell, "Now what?" The pillow talk is even more delicate at Joan's place. Having wound up in bed with William, Joan is unable to relax and consummate their On-again, off-again romance. William fears her reticence is "physical proof we don't belong together."

Joan runs into a figure from the past and makes a hasty decision that prompts Maya and Lynn to intervene.

Joan causes a dispute between herself and Aaron after purchasing an expensive kitchen range for their new house and not discussing it over with him. After they defuse their feud, Aaron receives unexpected news. Meanwhile, Lynn begins to flaunt her success with her progressing music career. Golden Brooks, Reggie Hayes, Keesha Sharp and Khalil Kane also star.