Lena, Gina, Charmaine, Dorian and Terrell decide to rent a house together. While seeing the temperamental landlord about a plumbing problem, Gina, Charmaine and Terrell discover that he is Langston "Sweet Knuckles" Paige, a former major league baseball star. He is unsure about what to do with his life, so they encourage him to enroll in college. Langston accompanies Terrell to class to check out the Hillman campus. He finds that the professor is an old flame. Gina's abusive ex-boyfriend Dion violates his probation by contacting her. He finally shows up in person in an attempt to win her back. She repeatedly turns him down, and learns that Dion hasn't really changed at all. Langston steps in and manages to convince Dion to leave Gina alone.

Legendary singer/actress Lena Horne visits the Hillman campus to dedicate a scholarship named for her grandmother. Whitley becomes very excited and has her students put together a musical tribute to Ms. Horne. She insists on a formal ceremony and refuses to allow Mr. Gaines to cater the event. Kim is mortified that Whitley could be so respectful of Ms. Horne, yet treat Mr. Gaines as though he is too old to contribute anything to society. When Ms. Horne admits that she doesn't like the upper-crust food, Kim takes her to the Pit for a home-cooked Southern meal. She has a good time dancing with Spencer, Kim and Mr. Gaines. Mr. Gaines recalls meeting Ms. Horne during World War II, and Kim is surprised to learn that this actually happened. During the ceremony, Ms. Horne calls Mr. Gaines to the stage and introduces him as an old friend. Whitley sees the error of her ways.

Vanessa is confident that her science project will bring her the usual top honors she expects, until she discovers that the other students in her new advanced-placement class are much more competitive than she thought.

After Sondra is ripped off by a conniving auto mechanic, an incensed Clair goes to court to right the wrong. While Clair is preparing her court case, Cliff plays family chef and cooks up some rather bizarre concoctions for dinner- leaving the kids hungering for Mom’s cooking.

Cliff is excited to join his former teammates from Hillman College in a grudge match against Norton University, until he discovers he is 25 years out of shape. Josh Culbreath, 1956 Olympic bronze medalist, guest stars as Sanford B. "Tailwind" Turner, the only man ever to beat Cliff "Combustible" Huxtable.

Clair is excited to learn that Cliff’s widower friend, Mike has a new woman in her life and invites the couple over for dinner. But Clair is shocked to discover that the beautiful Nikki is the same age as her oldest daughter.

As the girls reminisce in Synclaire's room the night before the wedding, a drunken Regine laments the fact that she hasn't been able to find a man. After Regine staggers off to bed, Max announces her intention to go buy some beer; but Khadijah and Synclaire are well aware of what she really wants. A defensive Max refuses to admit that her relationship with Kyle is serious. She meets him on the fire escape, where he shares the news that he has been offered the chance to head up a new office in London. She pretends to be unmoved, and claims that she is considering a partnership in Philadelphia. The next day, Khadijah fears that she and Synclaire will grow apart after she is married, until her cousin reminds her that she will still be in the building. Overton feels the effects of going 24 hours without food and faints. Regine is depressed when Russell shows up with a beautiful woman; and Max makes her feel even worse when she tells her that she was seeing Kyle, and that only Regine didn't know about it. Regine's prayers for a man are later answered when Super Bowl MVP Desmond Howard (Overton's cousin) asks her to dinner. Kyle takes Max aside in the hall to say that he enjoyed knowing her, as he has decided to take the job in London. As he turns away, Max says that she loves him. Regine whisks her away for the ceremony, leaving Kyle and Khadijah to deal with the shock. Kyle and Khadijah perform a gorgeous duet that he had written for the ceremony, and Kyle professes his love to a clearly moved Max as he sings to her. Overton and Synclaire are married, and stride happily down the aisle.

Kyle purchases a one-way ticket for Max in the hopes of persuading her to move to London with him. Max is furious that Kyle will not stay in New York for her, and accuses him of attempting to turn her into a housewife. Overcome with frustration, she trashes her friends' apartment; but later receives counsel from Khadijah and a surprisingly sympathetic Regine. Khadijah rejects Regine's snooty roommate candidate; then recruits Tripp Williams, an aspiring songwriter who has just been booted from Russell's apartment. Regine reluctantly allows him to move in on a trial basis, after initially claiming that having a male roommate would be a disaster because he would surely fall in love with her. A pushy activities director disrupts Overton and Synclaire's honeymoon cruise. After wandering off during a luau, the newlyweds discover that they have been left stranded on a deserted island.

Overton and Synclaire begin bickering about their predicament. They realize that much of their fear is the result of their anxiety about marriage, and vow to work together to overcome their doubts. A helicopter finally rescues the couple. The cruise director tries to force them to foot the bill, but Synclaire tells her off. Tripp quickly wins the affection of Khadijah and Max, but can't seem to do right by Regine. She attempts to break up his football-viewing party, but changes her tune when R&B singer Montell Jordan arrives. Although Khadijah warns that they are making a mistake, Kyle and Max refuse to re-consider their positions about his move to London. Khadijah drives Kyle to the airport, where they sadly say their good-byes. Max arrives at the last moment, and she and Kyle challenge one another to back down. As Kyle heads toward the gate, Max forlornly asks him for one last kiss. After a passionate kiss, Kyle departs, leaving a tearful Khadijah and Max to console one another. At the apartment, Max, Regine and Khadijah confer in the bathroom. They are shocked when Tripp passes by and exposes himself as he steps into the shower. Regine is the only one who seems to mind.

The Phoenix Suns come to town, and Max convinces Khadijah to visit the team's locker room and ask out Cedric Ceballos, with whom she has often flirted during interviews. Khadijah becomes so nervous over the date that she gets a splitting headache. Max tries to get her some aspirin, but accidentally gives her four herbal tranquilizers. (Regine had a supply so that she could give half a tablet to nervous brides.) Khadijah goes completely loopy at the restaurant, and refuses Max and Regine's attempts to help her. When they try to explain to Cedric, they are called groupies and thrown out. Tripp does not endear himself to the girls with his candor about Khadijah's situation. An old man comes by Overton and Synclaire's new apartment in the hopes of finding the old tenant, Mrs. Porchnik. Overton and Synclaire are afraid to break his heart by telling him that she has died. Max later tells him the truth (quite callously), and the man explains that Mrs. Porchnik owed him 500 dollars from a poker game.

When 20-year-old honor student Cathy Torrez doesn’t return to her Southern California home after her shift at a local drugstore, her mother immediately suspects something is amiss. But it’s not until her body is found a week later that police begin to dig into her private life, looking at boyfriends past and present, in hopes of finding a killer.

A beautiful nursing student is found shot to death inside her car. But this young lady isn't exactly what she seems, and soon detectives are knee deep in uncharted investigative territory, where sexual secrets explode with deadly consequences.

In Meriden, Connecticut Jennifer Helmedach falls for a bad boy with a short temper. After money problems, the two decide to rob a friend and it ends in tragedy. Then in Memphis, Lashonda Williams and boyfriend Roger Reed get wrapped in the seedy world of sex crimes that will eventually end in bloodshed.

Keeairra Dashiell was your typical girl next door until she met football star, Tyquan Knox; who tackled her heart and convinced her to do the unthinkable. Later, Shameeka Watson’s fiery temper leads her and her husband, Clarence McCord III, to commit a horrendous murder.

After falling mysteriously ill, Tiffani Jacobs is looking for a man to help her feel normal. But her dreams are shattered when the quest for true love drives her to do the unthinkable. And in Spokane, Washington, wild child Jackie Wortham scorches a path of destruction with a lover who fuels her fire.

Lena, Gina, Charmaine, Dorian and Terrell decide to rent a house together. While seeing the temperamental landlord about a plumbing problem, Gina, Charmaine and Terrell discover that he is Langston "Sweet Knuckles" Paige, a former major league baseball star. He is unsure about what to do with his life, so they encourage him to enroll in college. Langston accompanies Terrell to class to check out the Hillman campus. He finds that the professor is an old flame. Gina's abusive ex-boyfriend Dion violates his probation by contacting her. He finally shows up in person in an attempt to win her back. She repeatedly turns him down, and learns that Dion hasn't really changed at all. Langston steps in and manages to convince Dion to leave Gina alone.

Legendary singer/actress Lena Horne visits the Hillman campus to dedicate a scholarship named for her grandmother. Whitley becomes very excited and has her students put together a musical tribute to Ms. Horne. She insists on a formal ceremony and refuses to allow Mr. Gaines to cater the event. Kim is mortified that Whitley could be so respectful of Ms. Horne, yet treat Mr. Gaines as though he is too old to contribute anything to society. When Ms. Horne admits that she doesn't like the upper-crust food, Kim takes her to the Pit for a home-cooked Southern meal. She has a good time dancing with Spencer, Kim and Mr. Gaines. Mr. Gaines recalls meeting Ms. Horne during World War II, and Kim is surprised to learn that this actually happened. During the ceremony, Ms. Horne calls Mr. Gaines to the stage and introduces him as an old friend. Whitley sees the error of her ways.

Whitley has trouble getting through to a pupil that she is tutoring. Dwayne brainstorms about a video game that would get kids more interested in grammar. Ron suggests a game that combines grammar with the elements of baseball. Dwayne designs a computer program based entirely on this idea and pitches it to Kinishewa. Ron is furious when Dwayne refuses to share the credit (and money) with him. Dwayne accuses Ron of being a moocher always trying to profit from his accomplishments. Ron fires back that Dwayne resents his success as a club owner; and suspects that he feels inadequate after having to turn to Ron for money. Whitley suffers from chronic illness, and Kim forces her to confront the fact that she might be pregnant. A panicked Whitley refuses to accept the truth until she has taken a half-dozen home pregnancy tests. Kim assures Whitley that she will be a terrific mother, but Whitley doesn't know how she and Dwayne will come up with the money to care for a child. Dwayne reveals that Kinishewa has offered him a full-time job that will pay $80,000 a year. He is thrilled when Whitley announces her pregnancy. Dwayne explains that his new job comes with a catch: they must move to Tokyo. Kim finally accepts a marriage proposal from Spencer.

Marion and Adele arrive to help Dwayne and Whitley pack for the move to Tokyo. After learning of Whitley's pregnancy, they try to dissuade the couple from leaving. Whitley grows tired of listening to Dwayne argue with the women; she storms out. She finds solace with Ron, who has gotten into a major fight with Freddie over his plans to sue Dwayne. Dwayne convinces Whitley that they need to move on and make a life away from Hillman. Marion and Adele overcome their anxiety about being separated from their grandchild by getting very drunk. Dwayne and Whitley's friends throw them a going-away party at the Pit. Freddie comes over to Ron's apartment to share the news that she made law review. They make up, but she cannot convince him to come to the party. Everyone shares favorite stories about the Waynes and wishes them luck. Whitley and Dwayne return the favor by thanking their friends for all their love and support. Dwayne has very kind words for Ron, who hears about the speech from Freddie. He catches up to Dwayne moments before the couple is to leave for the airport. They apologize, and Dwayne offers to split the game's royalties. Ron suggests that he invest the money in the baby's future instead. Dwayne asks Ron to be the child's godfather. Dwayne and Whitley say goodbye, and Ron tearfully watches them depart.

Vanessa is confident that her science project will bring her the usual top honors she expects, until she discovers that the other students in her new advanced-placement class are much more competitive than she thought.

After Sondra is ripped off by a conniving auto mechanic, an incensed Clair goes to court to right the wrong. While Clair is preparing her court case, Cliff plays family chef and cooks up some rather bizarre concoctions for dinner- leaving the kids hungering for Mom’s cooking.

Cliff is excited to join his former teammates from Hillman College in a grudge match against Norton University, until he discovers he is 25 years out of shape. Josh Culbreath, 1956 Olympic bronze medalist, guest stars as Sanford B. "Tailwind" Turner, the only man ever to beat Cliff "Combustible" Huxtable.

Clair is excited to learn that Cliff’s widower friend, Mike has a new woman in her life and invites the couple over for dinner. But Clair is shocked to discover that the beautiful Nikki is the same age as her oldest daughter.

Max and Regine are surprised to learn that Synclaire has yet to sleep with Overton, even though they took the vacation to the Bahamas together. They encourage her to take the next step, but Synclaire is uncertain. She and Overton finally agree to have a romantic evening at his apartment the following night, as Kyle is out of town. After they experience a series of mishaps (including Overton's allergy to Synclaire's perfume), Synclaire admits that she is paralyzed with fear. She tells him that she is just not ready, and that she is feeling too much pressure from her friends. They decide to wait. Khadijah refuses to consider that her string of bad luck may have been caused by a broken chain letter.

Max takes a job as a telemarketer, unaware that her sleazy boss is a scam artist who sells subliminal tapes that do not contain subliminal messages. She is arrested while talking on the phone with Khadijah. Meanwhile, Overton sets up surveillance and begins recording all the girls' phone calls in the hopes of catching a prank caller. When the public defender assigned to represent Max proves to be woefully incompetent, she decides to represent herself. She points out that the boss was the only person to run, and cites this as evidence that the employees didn't realize they were committing a crime. She adds that she was making a personal call at the time that the police raided the building, and proves this through Overton's tape. The judge dismisses the case, and all the other employees ask Max to represent them. The judge recommends Max to the public defender's office, which hires her immediately.

Regine's doctor recommends that she undergo breast reduction surgery to alleviate her chronic back problems. After the surgery, Regine loses her self-esteem and begins throwing herself at men. Kyle assures her that she doesn't look any different, and states that her confidence and personality are what make her attractive to men. Kevon and the other neighborhood children blame Overton when a greedy ice cream man (who had been operating in the middle of winter) suffers a heart attack while reaching in the back of the truck for the Nutty Buddy that Overton had ordered.

Everyone is surprised by Regine's companion at Thanksgiving dinner--a charming, overweight parcel delivery guy named Darryl who does not meet any of image-conscious Regine's usual date criteria. When Scooter calls Khadijah and tells her that he wants to ask her something at the dinner, she and her friends believe that he is going to propose. She is shocked when he instead tells her that he has been offered a chance to manage a female R&B group and accompany it on a world tour. Scooter becomes angry when Khadijah does not offer her blessing. The group breaks off into boy and girl factions, who each rant about the opposite sex. When everyone re-assembles for dinner, Darryl's touching prayer prompts Khadijah to re-consider and allow Scooter to pursue his dream.

Kyle suggests that his firm take advantage of the untapped financial potential of Africa by creating a mutual fund, and volunteers to handle the project personally. Lawrence informs Kyle that the firm is concerned about using Kyle as a representative, as his appearance--specifically his hair--isn't "corporate" enough. Kyle does not want his career to be curtailed over such a trivial matter, so he considers getting a haircut. However, he then suffers a nightmare in which he turns into a jester who obeys his bosses' every whim (and is forced to dance before Queen Max). He calls a meeting and informs his bosses that his hair is a symbol of his pride in his African heritage. He had believed that the firm made its decisions based on merit, and will not compromise himself. Kyle learns that only Lawrence was worried about his hair, and that his concerns were dismissed. The African mutual fund is approved, and Kyle receives a promotion. Meanwhile, Khadijah is distraught when she continually misses Scooter's phone calls from the road. She finally realizes that she cannot put her life on hold while waiting for the phone to ring.

Khadijah's long-time friend Sheri accepts a job as a columnist at Flavor. She quickly makes friends with Synclaire, and the two go out to lunch every day and constantly joke around at the office. An annoyed Khadijah claims that their antics are disrupting the office, but she is actually very jealous. After she loses her temper and stomps off to her room during a game of Clue at the apartment, Synclaire confronts her. Khadijah apologizes and admits that she has been feeling left out. Sheri quits her job at Flavor, as she earned more money free-lancing. Overton suffers from insomnia after buying a new box spring. He does not sleep for days, and behaves erratically. When he goes upstairs to check on Khadijah and Synclaire, he falls asleep on Khadijah's bed.

After observing the depressing lack of talent at the cafe's open mike night, the group persuades Kyle to sing the following week. Overton agrees to perform his stand-up comedy act in exchange for Kyle's participation. Kyle starts out well as he performs "When I Fall in Love," but begins stuttering when Max enters in a low-cut gown and sits directly in front of him. He runs out of the cafe, thus ensuring Overton's victory. Max teases him mercilessly about his failure, while Overton believes that Kyle's unresolved feelings for Max are responsible for the incident. He urges him to get back on stage to prove himself. Kyle delivers a brilliant performance of "My Funny Valentine." He sings most of the song directly to a swooning Max. While the girls needle Max, Kyle thanks Overton for his advice, which he believes has freed him from Max's influence. At that moment, Max looks over her shoulder and smiles at Kyle seductively. He returns her gaze. "Oh Lord! There they go again!" Overton sighs. Regine tries an unusual method to help Khadijah overcome her fear of public speaking for an interview with Black Visionaries.

Khadijah hires Bobby Bonilla of the New York Mets to pen a weekly column for Flavor, just as her employees are poised to walk out over low salaries and poor working conditions. Bobby defends Khadijah, until he interprets her request for a hold on salaries as a salary cap (a major sticking point in the baseball labor dispute) and supports the strike. Khadijah insists that money is too tight to give raises, but Max warns her that she is on the verge of losing Flavor. Khadijah re-arranges her finances and agrees to give a modest salary increase. Inspired by a local video clerk's screenwriting success, Kyle and Regine try to pen an action/adventure screenplay.

A handsome young man from Synclaire's psychology class kisses her during a study session. Synclaire pushes him away, but is still gripped by guilt. She blurts out her indiscretion during a special evening Overton had planned for their first anniversary as a couple. Overton goes ballistic, storms out of the restaurant, and refuses to talk to her. Concerned for her cousin's well being, Khadijah sends Kyle up to the apartment to check on her. He finds Overton and Synclaire's clothes strewn throughout the living room. Meanwhile, Regine is livid when Max snags a coat she had left outside the apartment to donate to charity. Max begins wearing it constantly to spite her.

Overton and Regine get caught in a blizzard after he picks her up at the boutique. Max fears that she may be pregnant with "stand-by" boyfriend Michael's child. A concerned Kyle races to the store for a test, partially to get away from an ill-advised one-night stand--an annoying efficiency expert. Everyone is relieved when it turns out to be a false alarm. Regine receives word of the possible pregnancy when she calls the apartment, but cannot get the full scoop before the cellular batteries go out. Tired of Regine's whining, Overton finally slices up his precious bean bag chair and uses its contents for traction to get the van back on the road.

Regine suffers through a disastrous dinner with Darryl's closest friends, and realizes that she and Darryl don't have very much in common after he shares his dream of one day taking his wife on a cross-country fishing trip via RV. A panicked Regine heads to the bowling alley to seek advice from her friends; but Khadijah is flirting, while everyone else is caught up in Overton's pursuit of a 300 game. Regine's desperate cry for attention proves to be Overton's undoing. Regine and Darryl decide to break up, but agree to remain good friends. Max is forced to compliment Kyle constantly after losing a bet over the bowling game.

When Max's former flame Preston August becomes her new boss, they try to mix business and romance, but find that it is hopeless. They fail to get any work done, and each is insanely jealous when the other confers with co-workers of the opposite sex. They realize they must break up. Kyle is furious when a typo in his Flavor bio states that he is married, until he finds that being unavailable makes him more attractive.

Kyle grows weary of Synclaire's constant presence in his apartment, particularly after she ruins his iron by using it to make grilled cheese sandwiches, and scares away his date. He and Overton are at each other's throats, but have to talk things out when they get buried beneath Overton's new water bed (a suggestion of Synclaire's) while trying to prevent a flood. Khadijah and Max undertake a reconnaissance mission when a risqué video of Max dancing with a stripper at a bachelorette party accidentally ends up in Kyle's hands. Their plan goes awry when Regine fails in her role as lookout.

Kyle is thrilled when he is asked to serve as escort to a beautiful princess who is doing business with his company, but finds that security precautions cramp his style. Overton enlists the help of Khadijah and "secret weapon" Synclaire to gain revenge on a pair of pool hustlers. Regine exposes Max's jealousy concerning Kyle and the princess by claiming that the two are pictured in the society pages. She cackles when Max tears through the paper. Max announces that she will ease Regine's boredom by taking her along to watch Max get a tattoo, but her bravado fades considerably when she sees the needles.

Fabian realizes that Latrell’s new girlfriend is transgender and plots with the gang on how to break the news before he “seals the deal.” Imunique kisses him to sell the story that she broke them up because she was jealous. Meanwhile, Delroy and Macaroni Tony are on a roadtrip to Lake Tahoe and Delroy finds out Macaroni Tony used to date Bridget.

Imunique drives Latrell to his commercial audition and ends up landing the role he was going in for. After the commercial shoot, Latrell and Imunique have a huge fight… and end up in bed together. Meanwhile, Delroy has to finally get his first prostate exam.

In the season finale, Delroy pops the question to Bridget… only to find out she’s still legally married to Cordell’s father. When they get her ex to sign the divorce papers, he goes to the roof of Del Jones Realty where he threatens to kill himself. Meanwhile, Latrell and Imunique aren’t sure how to define their relationship when Latrell introduces her as his friend. Then, Imunique drops the bomb that she’s pregnant.