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.
Toni and Maya get into another argument before an evening out, in part because Toni refuses to believe that Maya can get the girls into an exclusive club. Toni tries to gain admission to the club and fails. Maya shows up and easily gets herself, Joan, Lynn and William past the doorman. Joan convinces the reluctant Maya to also get Toni into the club. When the doorman waves to Toni, another woman believes the wave was meant for her, and they get into an argument. Joan tries to play peacemaker, but the situation turns into a brawl. Maya and Lynn jump into the fight, but Toni is hurt by the fact that Joan fails to back her up. She begins to question their friendship, so Joan searches for a way to patch things up.
Joan begins dating a client, Frank Anderson. Everything seems to be going well until a crazed woman shows up at the office looking for Joan. She tells Maya and Lynn that she trailed her husband to Joan's house. Joan angrily breaks up with Frank in public. She later learns that Toni has been using her house to rendezvous with her married boyfriend and assumes that she was wrong to suspect Frank of wrongdoing. However, Toni's boyfriend soon delivers some surprising news that sheds new light on the situation.
Joan sees Maya's husband, Darnell, in a possibly compromising situation with another woman. Her gut tells her that something may be going on, but she agonizes over whether to share this information with Maya. Meanwhile, Toni begins dating a white city councilman who is also running for mayor. He becomes fascinated with her hair after she reveals that she wears a weave.
Maya and Darnell plan to renew their wedding vows, and Joan agrees to hold the event at her house. However, Joan constantly disagrees with Maya's choices and tries to mold the event into her own dream wedding. Maya tells Joan that she no longer wants her to be a bridesmaid, and later rebuffs her apology and takes her to task for constantly looking down on Maya. Meanwhile, Toni grows concerned by the tendency for black men to marry outside of their race. She determines that she and Lynn must do what they can to bring William ""back to the fold.""
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 turns to her friends for support when she fears that she might be pregnant. When a test turns out positive, she tries to cope with her fears about impending motherhood. Meanwhile, Lynn recalls memories of her ""white"" childhood after receiving a box of belongings from her mother.
The girls and William make lists of the qualities they want in their ideal partners. When everyone goes to an art gallery, Joan is amazed to find a man who meets all of her qualifications, but her friends later warn her that she may have frightened him with her aggressiveness. At the same gallery, Toni runs into an ex-flame who is tending bar; and William has another meeting with possibly unstable cop Yvonne and considers giving her a try. Lynn, meanwhile, becomes obsessed with a painting of a red triangle.
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.
Joan is upset when Sean must go out of town for Valentine's Day. Her frustration grows when she is unable to get in touch with him. Davis, who has recently reunited with his fiancée, stuns Joan by kissing her and offering to end his relationship to be with her. Maya, Toni and William spend the day with their significant others, and William frets about finding a card that doesn't send too strong a sentiment. Lynn volunteers for a suicide hotline and makes a date with one of the callers.
Joan decides to waive her ""three-month rule"" and sleep with Sean, but finds that the results are extremely disappointing. She seeks her friends' advice on how to help Sean improve his performance. Maya, with help from Toni, seeks medical attention after she and Darnell have difficulty conceiving a second child. William keeps having the misfortune of approaching every time Maya is discussing her gynecological situation with one of her friends.
After discovering that Lynn has applied for yet another grad school program, Joan and Toni determine that they must end their financial support and force her to get a job and go out into the real world. However, Joan has difficulty completely cutting Lynn off, leading Toni to conclude that Joan is an ""enabler."" Meanwhile, William encourages Yvonne to hang out with the girls so that he can have time with his guy friends; and Maya suffers from the side effects of hormone therapy.
Joan becomes fed up with the ""boys' club"" mentality at work, as her opinions are ignored and she is passed over for important cases. When she believes that William has deliberately stolen her idea, she blows up at him in front of everyone, leading to a rift between them. Meanwhile, Maya discovers that Toni and Lynn's yoga instructor is a little too ""hands-on"" in his approach toward his students.
Maya checks into the hospital to undergo surgery for the removal of a fibroid tumor. Joan's friends (especially Lynn) question her priorities when she decides to leave Maya's bedside to attend an important business dinner with Sean. Toni continues to clash with Greg over his lack of income. At the hospital, she takes an immediate interest in Maya's doctor, the wealthy and handsome Dr. Clay Spencer.
Toni cheats on Greg with Clay and winds up contracting chlamydia. Joan frets about the fact that Sean has yet to tell her that he loves her, especially after he reveals that he has been offered a six-month job in New York. She seeks her friends' advice on how to coax a love declaration from him. Meanwhile, Maya feels threatened by the temp who filled in as Joan's assistant during her absence.
Sean grows uncomfortable with Joan's relationship with Davis, as he feels that she flirts with him too much. After she confesses that they once shared a kiss, Sean upsets Joan by ordering her to stay away from Davis and 847 for good. Meanwhile, Toni angers Greg by displaying some of his paintings at the restaurant; and Darnell becomes impatient when Maya is reluctant to resume sexual relations with him after her surgery.
After Toni accepts Clay's marriage proposal, a disapproving Joan advises her to look into her heart, as she believes that Greg is the one she really loves. Toni comes to agree with her, and tells Clay that she cannot marry him. Unfortunately, in the meantime, Joan (unaware that Greg and Toni are even still together) accidentally tells Greg that Toni is engaged to another man, prompting him to dump her. Meanwhile, William issues an ultimatum to Yvonne after she is shot in the line of duty; and Maya continues to try to avoid having sex with Darnell.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
On the eve of their wedding, Yvonne learns that William hasn't told his mother about their relationship.
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.
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.
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.""
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.
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.
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.
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.
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.
Maya and Darnell seek marriage counseling from their minister. 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. Lynn finds work as a bartender, despite the fact that she has no idea what she's doing. William tries to prove to Swedelson that he has the toughness required to be a partner in the firm.
Maya's cousin Ronnie and his boyfriend, Peaches, tell Maya that they have spotted Darnell in a compromising position with a woman at the Red Lobster. It is the same woman that Joan once saw with Darnell years earlier. Maya confronts Cecily and learns that she is having an affair with Darnell. This leads the distraught Maya to declare that she and Darnell are now ""even"" and move back to the house, where she and Darnell make a decision about the future of their relationship. Meanwhile, William obsesses over the fate of a missing suitcase.
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.
Toni objects when Joan plans a birthday party for her. In the midst of their argument, Toni inadvertently reveals that she has been lying about her age for years. Joan and company tease Toni relentlessly about being older, and she grows insecure about her looks. After a disastrous Botox session, Toni seeks the advice of a plastic surgeon--whose only suggestion is therapy. Meanwhile, William winds up falling for a woman who was only supposed to be a one-night stand.
The girls instantly detest William's demanding girlfriend, Monica. Joan in particular is up in arms after Monica convinces William to renege on a promise to make her co-counsel for a big case because he would look better in the partners' eyes if he handled it himself. Joan seeks revenge on William, and the girls later confront Monica. Toni keeps running into plastic surgeon Dr. Todd Garrett. Although the two seem to have hit it off, Toni refuses to date him because of his lack of height.
After Lynn's unpaid loan has a negative effect on their credit, Lynn's parents pressure her to get a job and pay them back. Lynn's friends ""help"" her prepare for her interviews--by wrestling her to the ground and forcing her into a wardrobe change, as well as offering emotional support. Meanwhile, Maya hides the truth about her separation from Darnell from her mother.
Joan has several run-ins with an actor at the gym, but finds herself attracted to him. However, she re-considers her decision to date Ellis after discovering that he has lied to her. William's sister comes out to him, then asks him to become a sperm donor so that she and her partner can have a child.
Joan is excited when Ellis invites her to the premiere of his new movie, but he refuses to let her walk the red carpet with him (or sit with him at the film) because he wants to preserve his ""bachelor"" image. Ellis tries to make it up to her by doing a magazine interview with her. Meanwhile, Toni grows tired of client Laila Ali, who would rather hang out than do any house-hunting.
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.
William agrees to dress as Santa Claus on Christmas Eve in the hopes of restoring Jabari's belief in Santa (something that seems to concern Joan just a little too much). However, Monica arranges for him to host the annual Christmas party for the senior partners and important clients on the same night, and pressures him to blow off Jabari and his friends. As they argue, Monica makes a startling revelation about the way the met. Meanwhile, Todd gives Toni a unique Christmas gift: a doll of herself, which has a bizarre effect on her.
Lynn finds herself extremely attracted to a poet, and is stunned to learn that he has been celibate for five years. Ellis refuses to leave the house after fans on the Internet trash him and label him a sellout. William tries to win back the girls' trust following the Christmas Eve debacle.
Joan and William vie for a senior partner position, and are shocked when the firm instead brings in an outsider, Sharon Upton Farley. They plan to demonstrate their outrage by walking out, but only one of them follows through with it. Meanwhile, Lynn and Maya help Toni deal with her fears after Todd asks her to take an HIV test.
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.
Maya becomes depressed and lonely after moving into a new apartment, despite the presence of a handsome and friendly neighbor. Toni and Todd take her on a double date with a friend of his, with disastrous results. William takes Monica on a romantic Italian vacation, where he plans to break the news that he has quit his job. Sharon invites Joan to her book club, then proceeds to humiliate her.
Toni and Todd's relationship is thrown into flux after she inadvertently mentions marriage. When Toni goes into hiding, Todd seeks the assistance of her friends, who convince him that Toni loves him and help him confront his own feelings for her. Meanwhile, William finds himself extremely attracted to Sharon, leading to an odd face-off with Monica.
Joan becomes jealous over Toni's engagement, and takes out all her frustration on Ellis, whom she begins blaming for all of her problems. She also resumes training for the Los Angeles Marathon just weeks before the event in an attempt to take her mind off Toni. Intimidated by Toni's expensive registry, William, Lynn and Maya pool their resources to come up with a wedding gift.
Maya befriends a fellow single mother, a janitor at the law firm's building. They quickly make a connection, but Joan finds the woman's attitude irritating; and fears that her example could negatively impact Maya's relationship with Darnell. Meanwhile, William pretends to work at Lynn's office because he misses the camaraderie of a workplace; and Lynn tries to scam her co-workers out of money by pretending it's her birthday.
Lynn and Maya confront Joan about her jealousy and overall bad attitude regarding Toni's wedding. Joan is upset when Toni announces that Reesie Jackson, her college roommate, is coming to town to be a bridesmaid. Joan had forced Toni and Lynn to swear never to speak to Reesie again after she stole Joan's boyfriend, Brian. She is livid when she learns that Toni and Lynn have not only stayed in touch with Reesie, but are the godmothers of her two children. Joan gives Reesie the cold shoulder. She rants that Reesie stole her chance at a perfect life with a husband and kids. Reesie reveals that she has contracted AIDS from Brian. He had unprotected sex with men, refusing to take along condoms because he was in denial about the fact that he is gay. The girls try too hard to comfort Reesie, and freak out a little when she cuts herself while chopping vegetables. She assures them that they cannot contract HIV this way, but Joan initially remains a little skeptical. Toni picks out her
Maya makes her friends feel guilty about leaving her alone as they spend time with their significant others. She convinces them to accompany her to a hangout in her old neighborhood, where she runs into Darnell. She is disturbed to learn that he has failed to tell her that he has gotten a small business loan to open a car repair business, and by the fact that he has a new girlfriend. Meanwhile, William plans to return to the law firm, but first tries to complete a list of things he wants to do before he dies--including becoming a Soul Train dancer.
William and Sharon decide to continue their relationship, even after he re-joins the firm. Joan discovers that the two are together, and inadvertently blabs about it to Sharon in a moment of anger. Sharon breaks up with William, who shuts out Joan. Joan tries to rectify the situation, only to make things worse. Maya is desperate to find out what is going on when Joan fails to share the gossip with her. Meanwhile, Toni asks Lynn for tips for her wedding night.
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.
Toni's family comes to town, and Toni worries that her mother will embarrass her in front of Todd's parents by voicing her objections to their Jewish background. Mrs. Childs becomes dejected about the bickering between Toni and her older sister, Sherri--whom Toni refuses to include in the bridal party--and falls off the wagon. Meanwhile, William worries that he will lose one of his few male friends when the man begins dating Maya.
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
After nine months of celibacy, Lynn becomes fed up and grows suspicious of Sivad. She contacts his ex-girlfriend in the hopes of gaining some insight into his behavior. Meanwhile, despite her debt, Toni is determined to acquire a $17,000 bag. Joan and William try in vain to convince her to moderate her behavior and live within a budget.
Toni's brother Antoine comes to town for a weekend rendezvous with Maya, but soon spooks her by declaring his love and announcing that he will not return to Boston. When she rejects him, he locks himself in the bathroom and refuses to leave. Meanwhile, William orders Lynn to leave his house, but continually sabotages her efforts to find a roommate. Toni agrees to help Joan clean out her house, but insists that Joan's love life is what actually needs to be purged.
Joan finds herself in a bind when she is forced to agree to a dinner with both Ellis and Brock. She does not know how to handle the situation, although she insists that she is going to stay with Ellis. Joan winds up sharing a passionate kiss with Brock. Ellis nearly catches them in the act, and her friends witness the whole scene from the laundry room. Joan finally confesses her actions on the night of the play to Ellis. He is initially furious, but later visits her and lets her off the hook. They admit that they cared about each other, but were never really in love. Joan dashes off to give Brock a call. Meanwhile, William tries to cut a deal with Maya to get her to actually do her job, but she continues to outwit him.
Maya learns that tuition has increased substantially, and she doesn't have enough money to cover it. William tries to give her the money by pretending she has received it from the firm's continuing education plan, but she turns him down. Lynn housesits for Joan so that her DSL can be installed while she is away with Brock. Lynn claims that she is going to work on a grant proposal for another documentary, but gets nothing done. Joan refuses to let her stay at the house, and Toni and William also reject her. Maya agrees to let Lynn move in for a month if she pays rent. Lynn proceeds to lie around and do absolutely nothing. Maya pays her tuition, but learns that her credits do not transfer and she must start over again as a freshman. She is unbelievably frustrated and breaks down in tears. Lynn annoys Maya by complaining about her own plight and claiming to be depressed. William tells Lynn what Maya is experiencing and convinces her to be more sensitive, and also to take action
William convinces Joan to host a baby shower for his sister, Linda; and her partner, Kira. Kira's water breaks during the event. William wants to take her to the hospital, but they insist on having a midwife conduct a home delivery, which ends up taking place at Joan's house. Joan constantly worries that the water from the birthing pool will seep out and ruin her floors. Lynn drives everyone crazy as she suggests possible baby names and reads off their meanings. William fears that parenthood (and being a lesbian) is all just a phase for Linda, and they get into an argument. Linda threatens to keep William away from his nephew/son, so he says that he will not sign the papers relinquishing his parental rights. William's friends try to convince him to change his mind. He eventually apologizes and admits that the reality of having to sign away his rights had just hit him. He and Joan agree to have a baby together if neither is married or has a child in ten years. They soon come t
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.
Joan's enthusiasm about her new engagement is tempered when she learns that Brock doesn't want to have children, but she decides to relax and just focus on the immediate future. However, the issue continues to gnaw at her. Brock explains that, although his behavior may seem selfish, he believes it is wrong for someone to have children that they don't truly want. Joan tries desperately to change his mind; but he insists that they could be around kids by playing an active role in the lives of the children of family and friends. Joan ponders this for a while, but ultimately decides that she wants to have children of her own. Brock insists that they can have kids, but Joan fears that he would grow to resent her. They have a tearful break-up. William, determined to beat Joan to the altar, proposes to Lynn. He promises to support her financially and let her live at his place. Lynn learns that Joan and Brock have split, but keeps it to herself until after she has married William. Me
Toni is furious to discover that Todd failed to deliver a message from a remorseful Greg before the wedding. Claiming that she needs closure but actually hoping to rub her happiness in Greg's face, she insists that she needs to meet with him. Todd fears that Toni still has feelings for Greg and threatens to leave her if she sees him. Toni declares that Todd needs to trust her; she ignores his ultimatum and meets with Greg anyway. Meanwhile, Joan is devastated when William's nephew/son cries every time she holds him, as she sees it a a sign that she wouldn't be a good mother. After Jabari tells Maya and Lynn that his classmates think they are lesbians, Maya angers Lynn by saying that she wouldn't even be her type.
Maya invites Darnell's girlfriend, Lena, to her Christmas party in an effort to be civil. However, she grows jealous and gets Jalen to pose as her boyfriend. She is also furious when Lena gets Jabari a Game Cube (he wasn't supposed to get one because of his poor performance in school), and accuses the couple of not communicating with one another. Maya later catches Lena with a man at the bar, and winds up in the strange position of trying to help her with her relationship. Meanwhile, Joan gets really carried away while organizing a caroling outing for her friends.
A stranger stops Joan on the street and tells her, ""You made the right decision."" He claims to be a psychic, and manages to convince Joan that he is for real. She takes his words as a sign that she was right to break up with Brock. However, she soon re-considers after she runs into Brock on the street. She observes him playing with his young niece and concludes that she might be satisfied having children in her life without being a mother for a while. However, a visit to her gynecologist gives her pause when she is forced to face the fact that her child-bearing years are limited (because many older women face complications in their pregnancies). Meanwhile, a dream prompts William to confront Lynn about annulling their marriage. He accompanies the skeptical Maya when she tries to confront the psychic. After the man tells him that ""she's right in front of you,"" he mistakenly believes that he is destined to be with Lynn. The psychic later directs him toward a woman waiting for a
Toni refuses to believe Joan's claims that she isn't upset about spending Valentine's Day alone, and insists on constantly trying to cheer her up. She follows Joan to the movies and annoys everyone by talking loudly and giving away plot points. Joan gets up and moves to another seat, and runs into her old friend Davis. They go out to dinner and have a nice time together, but Joan realizes that she isn't ready to get into another relationship. Toni tells Todd that they shouldn't exchange Valentine's gifts because of their limited finances, but then reveals that she recently spent $2800 on boots. Todd is hurt when Toni then buys Joan a gift, but Toni actually realizes this and takes steps to correct her mistake. William tries desperately to make a connection with Donna, the woman at the bus stop, but she wants nothing to do with him. He makes the ill-advised move of sending Lynn to talk to her, which only ends up frightening Donna further. However, he later pleads his case and co
Joan's procrastination puts her job in jeopardy when she doesn't act quickly enough toward securing donations for a charity auction, which she has agreed to arrange for her boss. She turns to Toni to use her connections to the area's finer merchants to bring in an item that can help Joan meet the auction's $60,000 goal. However, Toni forgets to help Joan because she is obsessed with tracking down her ""best friend,"" supermodel Beverly Johnson (with whom she has never actually had any contact). Joan launches into a verbal tirade about Toni, which she overhears. Toni accuses her friends of being ""jealous, ugly bitches"" and continues on her quest to meet Beverly Johnson. She eventually meets Beverly, who is perplexed by her claims that they are soulmates and mistakes Toni for a schizophrenic. Toni reluctantly sees a therapist, where she initially raves about her life, but soon breaks down and admits that she fears no one would miss her if she died. Meanwhile, William seeks revenge a
Maya and her friends enjoy perks such as limo rides and entry to exclusive clubs, courtesy of her baseball player beau, Alex. She is reluctant to refer to him as her boyfriend, and bristles when he repeatedly makes up excuses to avoid spending time with her. She also objects when he surprises her with expensive new furniture. Alex convinces her to allow him to shower her with gifts, as he enjoys doing this and doesn't think of her as a groupie. However, when the girls show up at a party, Alex refuses to allow them to come inside. Toni forces Maya to face the fact that Alex only wants her as arm candy, to see when he sees fit while he continues to play the field. William continually bothers Alex for autographed memorabilia, while his friend Dan (who suddenly appears after learning that William knows a baseball star) can't seem to get the idea that Lynn isn't interested in him. Lynn, meanwhile, works on a documentary about single mothers. She pays them for their time by babysitti
Toni continues to see her therapist, Dr. Miller. Rather than following the doctor's advice and writing a letter to her mother detailing her grievances against her, Toni instead brings her mother to her sessions. Veretta stays with Toni and Todd and monopolizes the house. Todd tries to tolerate her rude and thoughtless behavior, but insists that she stop smoking in the house. Veretta refuses, and says that she doesn't have to listen to Todd because her daughter paid for the house. They get into a heated confrontation, and wind up ordering Toni to choose between them. Meanwhile, William worries that the fact that he and Donna have such different backgrounds (she cleans bed pans for a living and insists on travelling by bus) will impede their chances of having a future together. He vows to try his best to keep the relationship going, because he considers Donna to be special. Joan obsesses over whether to resume sessions with her own therapist after Lynn and Maya make several deris
Joan grows increasingly bored with her job. William notes that she doesn't hold the passion for the law that is required to truly succeed in their profession. She feels rejuvenated as she helps re-decorate Lynn's apartment. As Lynn returns some items she ""borrowed"" from her friends, Joan is furious to discover that Lynn forgot to send in Joan's application to the Fashion Institute many years ago. Joan had believed that she had been rejected, and had decided to go to law school because she didn't think she could make it as a designer. She lashes out at Lynn and blames her for changing the course of her life. Joan confides in Sharon about her dissatisfaction at work, and Sharon quickly takes her gripes to Swedelson. Joan assumes that she is about to be fired and tries desperately to get her job back. Much to her surprise, she receives a promotion. However, she realizes that her new success hasn't changed her feelings about her job, and decides to quit. Meanwhile, Maya receives
The newly unemployed Joan cannot stand the idea of just sitting back and relaxing, and drives her friends crazy by constantly cooking and knitting for them. She goes to the mall, and winds up taking a job at Wienercycle. Her friends tell her that this is a very stupid idea and convince her to quit. She tries to do this, but is inspired by the teenage shift manager's take-charge attitude and decides to stay and help her. Joan tries to defend her bizarre actions as the result of her work ethic, but experiences a wake-up call when she learns that the manager isn't really as gung-ho about her job as she had appeared to be. Meanwhile, William annoys Toni, Lynn and Maya by flaunting his new $6000 pen. Toni gets revenge by swiping the pen, and the girls enjoy watching William behave like a madman as he tries to find it.
Joan feels bad about the way the girls have treated William's past girlfriends and decides to go out of her way to make Donna feel welcome. She hosts a dinner to give them a chance to get to know her. 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. Donna confronts William during the ride home and offers the opinion that he is in love with Joan. He insists that this is not true and tries to provide reassurance. He then angers Joan by backing out of plans to do a song and dance together at the Cinco de Mayo party. Donna observes William's reaction to Joan's ridiculous performance and again opines that he loves her. William tells her about the psychic, but Donna believes that her purpose might actually have been to force William to face his true feelings for Joan. Meanwhile, the girls are furious when they
William is made a senior partner in the law firm. He is thrilled about this, as is Maya, who will now get a substantial raise. He brings a beautiful date to the party honoring his promotion. Joan comments that he now has everything he wants, but William still feels as though something is missing. He talks with Swedelson at a strip club. Swedelson says that William should not pursue a relationship with Joan and instead advises him to go after Sharon, who had earlier seemed to be sending William signals. However, William discovers that Sharon is involved with the building's security guard. He goes to Joan's house and tries to share his feelings with her, but backs down after she talks about thinking of him as her ""big brother."" Meanwhile, Toni, Maya and Lynn enjoy the benefits of an especially friendly masseuse.
Toni has an apparent breakthrough in therapy. When Dr. Miller asks with whom she would want to be stranded on a deserted island, she picks Joan and realizes from her explanation that it is because she loves her. She is excited to realize that she is capable of love. However, Todd is miffed when she explains this to him. He doesn't like the idea that she didn't know about love before, and sees her decision to choose Joan over him as another example of her tendency to not take his feelings into consideration. William tells Toni that she was wrong to talk about her session with Todd, and recommends that she do something to show how much she appreciates him. She plans to surprise him with a picnic lunch, but sees him dining with an attractive colleague and assumes they are having an affair. Although he insists that she is mistaken, Toni is worried, and the tension between them escalates. Maya completes her manuscript and asks Lynn to read it and give feedback. She asks her not to
Maya's neighbor, Jalen, tells her that he would like to begin dating. She turns him down because she feels that she has to much going on in her life for a relationship. Lynn expresses an interest in Jalen and asks Maya's permission to date him. Maya gives her approval, but then confesses to Joan that she only did this because she is sure that Jalen will reject Lynn. Much to her surprise, Lynn and Jalen being seeing each other. A jealous Maya continually makes up excuses to barge in and try to break up their date. She eventually admits that she is interested in Jalen. She and Lynn ask him to choose between them, but Maya fears the repercussions on their friendship. They decide that neither of them will date Jalen. Todd tells Toni that he has been offered a job interview in New York. He is very upset when she tells him to go for it without even asking him for any details. He gets the job as a plastic surgeon on a reality show, and tells Toni that he doesn't want her to come wi
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
