Kim tries to keep her grades up while juggling a hectic schedule. Col. Taylor takes in Mr. Gaines after Velma kicks him out because of a disagreement over their son.

Freddie is interested in a star baseball player Garth Parks, but when Dwayne finds out Garth's past indiscretions he warns Freddie who disregards his warnings thinking he is jealous.

While leafing through a catalog, Clair sees that a painting by her great uncle is for sale at an auction. S he remembers her childhood when the painting hung in her grandmother's house, but was later sold to pay medical bills. Although the estimated price for the painting is very high, Clair is determined to bring it back into the family. John Marion, head of Sotheby's, the prestigious New York auction house, guest stars as the auctioneer.

With an exam on Shakespeare's “Macbeth” less than two days away, Theo and his friend Cockroach scheme to pass the test without reading the play. Meanwhile, the Huxtables enjoy some new-fallen snow by having a snowball fight, and Cliff takes Rudy sleigh riding.

The Huxtable family dentist, Dr. Burns (played by guest star, Danny Kaye), helps Rudy's friend, Peter, overcome his fears of dentists with his zany style of dentistry. And Peter isn't the only patient persuaded by Dr. Burns to jump into the chair as Cliff gets a checkup of his own.

Cliff convinces his father, Russell, a former professional musician, to come out of retirement and play with his old band, The Jazz Caravan, in an old-fashioned jam session. Since his retirement, Russell thinks he's not the musician he used to be. But Cliff and his mother, Anna, use reverse psychology to convince him to blow the trombone with his pals once again.

Khadijah, Regine and Synclaire are involved in a car accident with an old woman named Shirley Shortridge. Khadijah's jeep suffers $1500 in damage. Regine believes that they should sue, but Khadijah wants to settle and put the matter behind her. Khadijah and Max negotiate with Shirley and her sleazy lawyer, Jack Peabody. Khadijah ignores Max's advice and agrees to take an $800 settlement. Jack taunts Max, telling her she couldn't have beaten him in court. Max decides that the case should go to court. When Max becomes obsessed with victory, Khadijah decides to represent herself and ask for the settlement. Jack denies offering any money. Max comes to the rescue, taking over as Khadijah's lawyer and winning a $1500 settlement. Overton and Kyle take a trial membership at a gym, but suffer the consequences when they overdo it on the stair master and Kyle tries to impress two women with his weightlifting ability.

Regine begins dating a single father named Patrick. She gets along wonderfully with his adorable daughter Camille, and agrees to spend the day with her while Patrick is away in New Jersey on business. When Patrick is delayed, Camille spends the night at the apartment. She suffers from a stomachache, and Regine runs herself ragged trying to care for the girl. Regine tells Patrick she is not ready to be a mother, but he urges her not to worry, as they are a long way from taking this step. Kyle becomes a Big Brother to a young boy named Kevon, but the boy prefers spending time with "Uncle Obie" to Kyle's dull, educational outings.

Khadijah's old friend Scooter comes to town, and the two begin spending a lot of time together. Although Khadijah insists that they are only friends, she ends up spending the night with him. When Scooter asks her to come out to his Los Angeles home for the weekend, Khadijah's friends offer conflicting advice. Max believes she should go for it, while Regine warns that she could destroy her friendship. Khadijah decides that she isn't ready to take such a big step, and asks for time to re-evaluate the relationship. Overton helps Synclaire study for her accounting exam in the hopes of making time with her, despite the fact that he knows nothing about the subject. He is discouraged when Synclaire (following Khadijah's plight) announces that she would never date a friend.

Synclaire is angry when she is passed over for a promotion. When Khadijah asks her to define the type of job she is seeking, Synclaire's friends help her to realize that she would like to become the office manager. Khadijah insists that Synclaire cannot handle such a responsibility. She adds that, given Synclaire's frequent blunders, she probably would have been fired if she weren't the boss's cousin. Synclaire quits in a huff, and lands a job at Turkey Hut. Synclaire's replacement at Flavor, Mrs. Ryan, is efficient but extremely cold and impersonal. When Synclaire comes to the office to retrieve her belongings, she helps Mrs. Ryan find a file by explaining that her filing system is based on emotions. Things that will make Khadijah happy are in the front of the cabinet, while those that will upset her are hidden in the back. Khadijah realizes that Synclaire's sweet, cheerful personality makes up for her incompetence. She re-hires her as Vice President of Office Affairs (she had already quit the Turkey Hut after learning the contents of the turkey nuggets), and allows her the honor of firing Mrs. Ryan.

When Air Force veteran Michael Giles departed the military to begin a quiet life in the suburbs of Dallas, Texas, he soon finds himself stalked by a figure from his past.

Jacklyn Miller and Richard Dickerson seemed to be the perfect couple and shared a passion for styling hair. When Jacklyn goes missing, the investigation uncovers a series of lies.

In Kansas, teen Eboni Fingal is destined for greatness. But her promising future is put in jeopardy when she falls for the wrong man. Later in Maryland, Larlane Pannell-Brown has the perfect life and husband. But when she gets involved with a younger man, she will do anything to hold on to her new love.

Tennessee native Vanessa Claude falls for a man with a devious plan. But when she agrees to help him, she ends up having a night she’ll never forget. And in Calumet, Illinois, Mary Ann Arnold refuses to share. So when another woman takes an interest in her man, she’ll move hell on earth to keep her at bay.

Maryland mom Kimberly King struggles financially while raising her two children alone. But when she falls in love with a younger man, her infatuation blinds her to his cruelty and greed. And in Covington, Georgia, orphan Brittney Beasley will stop at nothing to secure her and her lover’s future.

Kim tries to keep her grades up while juggling a hectic schedule. Col. Taylor takes in Mr. Gaines after Velma kicks him out because of a disagreement over their son.

Freddie is interested in a star baseball player Garth Parks, but when Dwayne finds out Garth's past indiscretions he warns Freddie who disregards his warnings thinking he is jealous.

Freddie is interested in a star baseball player Garth Parks, but when Dwayne finds out Garth's past indiscretions he warns Freddie who disregards his warnings thinking he is jealous.

Rev. Jesse Jackson comes to Hillman for a lecture and encourages Dwayne in his campaign for student council president. Freddie is excited about her 18th birthday.

While leafing through a catalog, Clair sees that a painting by her great uncle is for sale at an auction. S he remembers her childhood when the painting hung in her grandmother's house, but was later sold to pay medical bills. Although the estimated price for the painting is very high, Clair is determined to bring it back into the family. John Marion, head of Sotheby's, the prestigious New York auction house, guest stars as the auctioneer.

With an exam on Shakespeare's “Macbeth” less than two days away, Theo and his friend Cockroach scheme to pass the test without reading the play. Meanwhile, the Huxtables enjoy some new-fallen snow by having a snowball fight, and Cliff takes Rudy sleigh riding.

The Huxtable family dentist, Dr. Burns (played by guest star, Danny Kaye), helps Rudy's friend, Peter, overcome his fears of dentists with his zany style of dentistry. And Peter isn't the only patient persuaded by Dr. Burns to jump into the chair as Cliff gets a checkup of his own.

Cliff convinces his father, Russell, a former professional musician, to come out of retirement and play with his old band, The Jazz Caravan, in an old-fashioned jam session. Since his retirement, Russell thinks he's not the musician he used to be. But Cliff and his mother, Anna, use reverse psychology to convince him to blow the trombone with his pals once again.

Synclaire is offered a role in a play about a group of strangers waiting for an ATM. The quirky director decides that the perfect ending for the play would be for Synclaire to scamper across the stage in the nude. Synclaire is unsure about showing her "ta-ta's" on stage, but Overton tells her that the decision is hers alone. Synclaire is prepared to back out of the play, but changes her mind when she sees a poster that refers to her as the star. Max refuses to believe that Khadijah is friends with Vinnie of the rap group Naughty By Nature, even after Regine confirms her story. (She says that Vinnie used to look up Regine's dress and made her eat flies when they were children.) Max mocks Khadijah when she can't get in touch with Vinnie, but is speechless when the group shows up on Khadijah's doorstep. Max hits on Treach, but finds that he is "too freaky" for her, and the group agrees to attend Synclaire's play (after learning there is nudity involved).

Khadijah vies with Marcus Hughes, a pompous reporter from the Village Voice, to break a story about a promoter who fixes fights. Khadijah appears to have the upper hand when she coaxes one of the fighters into granting an interview and providing details of the scandal. Marcus tricks the maid into letting him into Khadijah's hotel room, where he hides in the bathroom and records her interview. However, Khadijah has one more trick up her sleeve: she arranges for Flavor to hit the newsstands a day earlier than usual. She taunts Marcus by noting that he may work for a big magazine, but Khadijah calls the shots at Flavor. Regine is thrilled to discover that she is the inspiration for a popular doll. Max convinces the toy company to give Regine a share of the profits, but Regine's dreams of wealth are dashed when a defect in the doll is discovered: its wig is highly flammable

Khadijah and Regine send their mothers to the Bahamas as a Mother's Day gift, and Khadijah's grandmother comes to stay with her. Rita expresses concern about the fact that Nana has been wandering off, and fears that her age is showing. Nana vanishes, and Khadijah is stunned to find that she has returned to New Jersey for a rendezvous with her boyfriend, the town baker. With Khadijah as a buffer, Nana finally has a talk with Rita about her need for a personal life. After Laverne reminds her about her affair with a snorkel instructor, Rita agrees to give Nana a break, provided that she be more honest in the future. Overton videotapes the events as a gift for his mother. While researching his family tree, Kyle discovers that his great-great-grandfather invented the sipping straw, only to be bilked out of his money by a hustler who was one of Max's ancestors. Kyle has the last laugh when he learns that the pain of losing their fortunes was what first brought his great-great-grandparents together.

Thanks to Synclaire's letter, the talk show Delia invites the roommates to appear in a segment entitled, "Roommates From Heaven, Roommates From Hell." While the "roommates from hell" end up sobbing and hugging one another, the girls are in danger of being bumped because they are too happy, and thus, not interesting. Regine tries to liven things up by speaking of her roommates' faults and portraying herself as the glue that holds everything together. A furious Khadijah blurts out that she only asked her to move in because Laverne begged Rita to help her daughter find a place to live. Regine is humiliated, and feels unappreciated. Khadijah assures her that she has grown to accept her quirks, but Regine does not want to stay where she isn't wanted. She decides to move out. Khadijah, however, is certain that the whole thing is just another ploy for attention.

Regine begins the process of moving out of the apartment. Khadijah and Synclaire interview a prospective new roommate, an obnoxious woman who smokes and has creditors on her tail. In spite of this, Khadijah is willing to give her a try--until she insults Regine. Unable to cope with the tension, Synclaire begins to display as many traits of a nicotine addict as are possible without actually smoking or chewing tobacco. She pleads with Khadijah to apologize to Regine and ask her to stay. Just as Regine is about to depart, Khadijah breaks down and apologizes. Regine refuses to reconsider, as she believes that it is time for her to move on. Khadijah slams the door in her face. Meanwhile, Max is actually purchasing groceries when the store is held up. Kyle stumbles through the door and subdues the man. Max is certain that he has saved her life. She runs across the store and flings herself on him, and later offers to cook him dinner as an expression of her gratitude. Kyle confesses to Overton that he is no hero; he simply stumbled into the man in his haste to buy some Kaopectate. He breaks the dinner date, as he doesn't want to take advantage of Max. She orders him to attend. After Kyle confesses the truth about the robbery, Max admits that there may be other reasons behind her dinner invitation. They confess to a strong mutual attraction. Max fears that they are moving too fast, and isn't sure that anything is going to happen, but she and Kyle end up sharing a passionate kiss.

Regine shows up at the laundromat, despite the fact that it is nowhere near her new apartment. She and Khadijah are less than civil, and Regine won't admit that her new place is a dump in a bad neighborhood. She invites everyone except Khadijah to a housewarming party, but Max declares that she and Kyle will boycott the affair. An annoyed Kyle goes without her. Max convinces Khadijah to crash the party. Kyle calls Max to task for her constant struggle for control within their relationship, but their passion is rekindled after he reveals that he saved her some shrimp and cocktail sauce. Everyone becomes a little disturbed by the fact that Regine's new neighbors hold personalities eerily similar to those of her old friends. Khadijah and Synclaire believe they have located the perfect roommate, but Regine interrupts their conversation on the fire escape. She reflects on her long friendship with Khadijah, and admits that she feels lost without her. They patch things up and return to the brownstone.

Overton is mortified when he sees Melody, the woman who once shattered him by rejecting his marriage proposal, at the hardware store. He sneaks out, but she later gets his number from his friend Pug and gives him a call. Although Synclaire feels that it is a terrible idea, Overton agrees to meet Melody at Cheezy Burger. After Kyle inadvertently tells her about the proposal, a furious Synclaire tries to retaliate by driving to Bayonne to meet up with a man who sends her a Christmas card each year. She learns that he is an insurance agent, not an ex-flame. Melody tells Overton that she has come to appreciate him, and that she is now willing to spend her life with a "simple" man. She tries to kiss him, but Overton (who was once powerless to resist her advances) now feels nothing for her because of his love for Synclaire. Regine is annoyed to find that Khadijah and Synclaire have re-decorated the apartment and forced her into the worst bedroom, but is cheered when she discovers that her new room has free premium cable.

NBA star Grant Hill comes to town for a Basketball/Piano Camp, and agrees to an interview for Flavor. While playing a game of one-on-one against Khadijah, he injures his knee in a mid-air collision. Khadijah feels guilty, but the injury is not serious. Grant comes over to the apartment, and he and Khadijah end up kissing (much to Regine's horror). Although Grant sweeps Khadijah off her feet and is interested in a relationship, Khadijah feels that the distance between them and their busy schedules would make this impossible. She breaks up with him, as she doesn't want to get hurt. Synclaire and Max suggest that she still hasn't gotten over Scooter. Kyle and Max are frustrated beyond belief when they cannot beat Overton and Synclaire at a single board game. Overton and Synclaire finally throw a game of Battleship to shut them up. A college-age messenger delivers a package to Flavor and is instantly smitten with Khadijah.

Kyle grows increasingly surly as his 30th birthday approaches. Max, at her friends' urging, throws him a surprise party. He does not wish to participate, but is coaxed into a game of Barnyard Twister. Kyle throws his back out and leaves, humiliated. Max finds him sulking at the laundromat and asks him what is wrong. He explains that he has failed to meet many of his professional goals. Whereas he had always been a wunderkind, he now feels that he is going nowhere. Max tells him that there are some good things to be said for aging. She points out that he never could have gotten her into a relationship if he were still as immature and sexist as he was when they met. She says that she is giving herself to him for his birthday. Kyle thanks her, laughing that she is "sweet and cheap." Synclaire fills the house with plants, and is distressed when they die after just two days. Khadijah feels that Synclaire was smothering the plants with attention, and jokes that they committed "planticide" to get away from her.

Regine is thrilled when a famous designer purchases the boutique, until she learns that he has decided to target the mainstream market and convert it into a discount store called Le Rag Bin. Although her mother can't get enough of the merchandise, Regine is on the verge of quitting when she assembles a particularly gaudy outfit for one customer. The woman is actually a wardrobe consultant for the hit soap opera Palo Alto. She is impressed with Regine's ability to perceive what is tacky, and hires her as her assistant. Meanwhile, Overton is mortified to learn that he is a dead ringer for a porn star.

Khadijah and Synclaire learn that a $500 savings bond they opened as teenagers has matured, and is now worth $2700. Khadijah is anxious to use all the money to purchase a new computer for Flavor, and doesn't realize that Synclaire wants to use her half to attend a Harvey Keitel acting seminar. Synclaire spends her money without consulting Khadijah, who is unaware of her actions until the new computer is repossessed. Khadijah spends her share on a raise for Russell, and is furious at her cousin. She later learns that, although she had always considered Flavor their dream, Synclaire does not feel this way. She agrees to support Synclaire's aspirations. Kyle is outraged when he learns that Max has one more name in her little black book than he does. Max accuses him of being childish, but he isn't pacified until he discovers that he hasn't included Max in his book, while he is in hers.

Overton is devastated when a bookshelf he built falls apart and kills an ill-tempered cat that Synclaire was watching for an acquaintance. Overton tries to make amends by building the cat a beautiful coffin, but this also falls apart. He decides that he has lost his skill as a handyman, and takes a job as a bartender. Synclaire and Kyle cannot change his mind, but he eventually learns that the accidents were the result of faulty glue that has since been recalled. Meanwhile, Max is devastated by the news that she is allergic to chocolate, and is subjected to much taunting from Regine.

Kyle fears that his firm's new client, esteemed actress Jacqueline Richards, is coming on to him. He makes a fool of himself trying to reject her advances. She assures him that she only wants to be friends, but Kyle feels as though he is her lackey when she buys him gifts and takes him to expensive restaurants in exchange for errands. He draws the line at cleaning up after her poodles. Kyle agrees to be her friend, but tries to help her realize that true friendships are not based on monetary compensation. Khadijah is embarrassed when L.O.O.F.A., a children's group for which Synclaire volunteers, names her its hero of the year, on the basis of a lie she once told Synclaire about pulling a man from a burning car during their youth. Khadijah saves the man from choking after the ceremony, but Synclaire doesn't believe her.

Scooter returns to New York, but receives a chilly reception from Khadijah, who is furious at him for failing to call her for months. They are arguing on the roof when Scooter suddenly flashes a ring and proposes. Khadijah accepts immediately. Both quickly begin to experience doubts about the upcoming nuptials. While at the jewelry store to size the ring, they realize that they only got engaged because they were afraid of losing one another. They were not ready for marriage before Scooter's departure, and spending a year apart certainly did not strengthen their relationship. They call off the engagement and decide to go back to being friends. Regine, in the midst of a dating dry spell, follows her friends' advice and nixes a date with carpet cleaner Cleophus Wade when he asks her out over the phone. She is disgusted to learn that Cleophus is handsome and wealthy (he owns the company). He thanks her for rejecting him, as this pushed him into reconciling with his ex-girlfriend, whom he takes to expensive restaurants and lavishes with gifts.

After Imunique screws up at work, Delroy fires her. Jasmine immediately starts being overwhelmed at all her new duties, only to find out that Imunique has been sneaking into the office and sabotaging everything. Jasmine is finally able to get Delroy to apologize and hire her back.

Delroy and Bridget become friends with an overly-friendly couple, Ron and Tina… who turn out to be swingers. Meanwhile, Latrell tells a joke on stage that was written by his “little brother” Jalen. After the joke is a success, Jalen sues Latrell for joke jacking.

Imunique fights off a burglar and becomes a local celebrity. However, when the police want her to identify the guy, she isn’t sure she wants to rat. But when the burglar attacks Ms. Earleane, Imunique has a change of heart. Meanwhile, Delroy teaches Jasmine how to close deals… but she ends up teaching him a thing or two.