Five months later, and Moesha still hasn't returned home. After Kim forgets to purchase tickets to a sold-out concert featuring R&B singer Brandy, Moesha decides to spend her weekend alone with her new beau, Aaron, a college student whom she met over the summer. But when Moesha starts to push the relationship further (mainly due to her strange suggestions), the two break up. Later, Moesha, Kim, Niecy and Hakeem attempt to get into the concert. Backstage, Moesha meets Brandy who gives her some advice.
Without Moesha around, Myles begins to miss his sister. Moesha helps her friends with their Homecoming preparations. Grandma Mitchell visits the family and stirs up a heated conversation over Moesha and Frank's disagreements. Myles tries to make an attempt to keep the family together (reminiscent to the 1997 movie Soul Food). After all the hostility dies down, Frank tells Moesha that he wants her to return home.
When Frank and Dee find a marijuana cigarette in the house, all suspicion leads to Moesha. After wrongfully accusing Moesha, they are all shocked to learn that the joint belonged to Myles.
Dee convinces the family to join Myles in a family therapy session, but Moesha decides to ditch the session to hang out with her friends. Frank reschedules the session so that everyone can attend and everyone begins to open up and express their feelings towards one another.
A new teacher starts work at Crenshaw High, and Moesha makes a bold move and kisses him. Worrying about the consequences involved between teacher-student relationships, Channing decides to leave Crenshaw High for good.
Moesha, Kim and Hakeem think a bully named Devon Stamps, from their third grade class, is stalking them, due to a practical joke that turned ugly.
Musical guest: Big Pun Moesha and her friends visit Charisse, Moesha's cousin, at Maynard University during Prospective Freshman Weekend. While there, they tour the entire campus and meet new friends (Iris and Mervin) as well as Moesha's ex-boyfriend Aaron. Old sparks flame again for Moesha and Aaron, but she becomes more interested in Mervin. Later, Mervin slips Moesha a drug in her drink, but Aaron comes to her rescue. Meanwhile, Myles has a slumber party.
Now that they're a couple again, Moesha tries to discover what true love is all about. Niecy reveals that she's the first out of the group to have sex; prompting a curious Moesha with various questions about love and sex. Moesha and Kim visit the health clinic where Moesha prescribes for birth control pills. Later, Dee finds the pills in Moesha's purse; leading to a serious conversation about sex. Dee promises Moesha that she won't tell Frank about the pills. Moesha meets Aaron but her anticipation for a romantic evening turn into a nightmare when she learns that he has had many sexual partners. Upset, Moesha walks out of his life for good.
Moesha and Hakeem are bummed to learn that Eddie have them working on Christmas Eve. She tries to find a good excuse so that she can finish her last-minute shopping. An elder man visits the store to apply for a job, but Eddie tells him that they haven't hired anyone new in awhile. Later, the unemployed man is now dressed as Santa Claus and holds the entire store hostage.
Andell holds a tutoring program at The Den, and Moesha decides to write an article about the tutoring sessions in hopes of winning a newspaper's journalism contest. One of Myles' friends named Justin reveals a story that he has trouble reading (only so he can be around Moesha). So, Moesha decides to write a story on Justin's illiteracy but she forgets one important thing-- she didn't check the facts after Justin lied about not being able to read. Meanwhile, Frank goes on a diet after he becomes slightly overweight.
During Black History Month, Moesha and students divide along racial lines after a protest over the lack of black representation in Antonio's mural of Mexican-American migrant workers. Meanwhile, Myles tries to win a new bike in a contest.
Musical guest: LeAnn Rimes Moesha and Kim have a fight over Kim's unprepared college plans. Later, MTV's ""FANatic"" picks Moesha to escort Kim to meet country singer LeAnn Rimes. LeAnn Rimes gives Kim and Moesha some good advice on how to remain good friends. Meanwhile, Hakeem accidentally sees Dee naked.
Moesha and her friends participate in The Ladies of Eminence Debutante Ball, but Moesha has second thoughts because she's not interested in ""high-class society."" But she changes her mind when she learns that her former classmate Mary Ellen Hobbs is banned from the affair after getting pregnant.
Moesha's singing dilemma is illustrated in a 1950s-style sitcom episode, a la ""I Love Lucy,"" about an audition for a Broadway revue.
Moesha is envious of a gifted, yet reclusive, classmate who is named valedictorian but she also learns that he's homeless and cleans tables in the school's cafeteria. Meanwhile, Frank thinks Myles is ready for the ""talk.""
Moesha throws a slumber party with her girls, Kim and Niecy, to reflect on the good times they've spent together before they leave for college.
In this Parker's spin off episode, Kim's mother returns to high school with her after leaving 18 years ago. Nikki is looking to receive her high school diploma and head to college with Kim. This episode serves as a back-door pilot for the spin-off series "The Parkers" (1999) focusing on Kim Parker (Countess Vaughn James) and her mother Nikki (Mo'Nique).
Musical guest: Johnny Gill After Andell thinks her relationship with Bernie is headed nowhere, Earl Thomas, Andell's college boyfriend, returns to rekindle the flame by proposing to her. Meanwhile, Frank overreacts to Dee's urge to keep a picture of a young man from her past.
Moesha meets the boy of her dreams at her prom and shares a romantic dance until he dashes off mysteriously. She spends the next day combing through yearbooks to find this mystery man who turned out to be an employee at the hotel where the prom was being hosted.
Moesha turns 18 and the gang decides to throw her a surprise birthday party but Kim spoils it by telling her. But the real surprise for Moesha is when all her former boyfriends, Ohagi, Q, Jeremy and Aaron, all stop by to show how they all want her back. But Moesha doesn't want to start over with any of them- except for her former teacher, Channing. After realizing that a relationship between them wouldn't work, Moesha and Channing both decide to just remain friends.
Moesha, Hakeem and Niecy go across town for a graduation day brunch where Moesha's car breaks down an hour before the big event. After finding many solutions to finding a way to their graduation, Moesha, Hakeem and Niecy finally make it across the stage. But Moesha's post-graduation plans change when she gets a job offer with VIBE magazine.