Regine moves back into the brownstone, but the girls have made some changes to the apartment. Overton gets a visit from an ex-girlfriend who he previously proposed to.
Khadijah injures Grant Hill in basketball. He goes to her house for an interview and he asks her on a date. Max and Kyle can't beat Synclaire and Overton at any game.
Overton and Kyle attend a bachelor party where they see an adult film with the star of the film being the spitting image of Overton. Regine's boutique gets bought out and she gets a new job title that she's not too happy about.
Synclaire and Khadijah's childhood savings bond matures and they get a check, but they have differing opinions about how the money should be spent. Max hides her black book from Kyle and Regine finds it.
Overton gets a chance to take a half-court shot to win some money. Max steals Regine's homemade dress for a fancy banquet, but she doesn't know it was made as a tear away.
Khadijah finds Dean Cain's wallet and won't release it to anyone but him. Max's mom comes for a visit and says she wants to have a closer relationship with Max.
A discouraged Synclaire is unsure about auditioning for an infomercial for a dashboard grill, but Max encourages her to follow her acting aspirations. Regine volunteers Max to drive Synclaire to the audition in order to keep her from hanging around the apartment on her day off. Max confronts the director when he dismisses Synclaire without allowing her to say her lines. Meanwhile..Overton is racked with guilt when he continually dreams about the R&B group TLC after falling asleep during its videos.
The gang takes a trip to the mountains for Christmas. Overton is disappointed when a mountain ranger doesn't let him keep up with his family's Christmas traditions.
Khadijah wants Max to write a legal editorial for "Flavor" and they bump heads on what Max writes. Synclaire wants Regine to use her influence to get her a part on her soap opera.
After Khadijah's errand gets Ivan fired from his messenger job, she hires him at Flavor. He doesn't check his facts and causes Khadijah to print a bogus story. Overton is upset when his friend chooses Kyle to be his baby's godfather instead of Overton.
Regine is dating a handsome weather man. She visits him one day at work and on her way out, she bumps into a charming older man who asks her out. Later, she finds out they are father and son. Kyle helps the rest of the gang invest their money in stock.
Maxine and Kyle breakup after she sends him on a date with another woman. Russell is in danger of being deported and asks Khadijah to help him stay in the country.
Overton's favorite uncle, Tibby, tells Overton to dump Sinclair because she is too upbeat. Kyle gives Max an engraved bracelet that he bought for her before they broke up.
Khadijah sees a therapist to help with the issues of her life. Synclaire and Kyle try to help Overton overcome his fear of clowns when Synclaire takes a job as a clown.
Reverend Taylor asks Kyle to speak to a group of teens on how to become successful. Max tests Regine's statement that she doesn't care that Keith paints nude portraits by offering to poses for one.
Regine's mother catches her and her boyfriend, Keith, in a compromising position on the roof. Overton finds the perfect ring for Synclaire, but has to track it down when someone buys it before him.
