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 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.

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.

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.

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.

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.

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.

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.

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