Dwayne is selected for Phi Beta Kappa, and his mother comes to town to watch his induction ceremony. Julian tells Whitley that he wants to ask her something important during their next lunch date, leading her to believe that he plans to propose. He instead asks her to spend the summer with him in Washington, D.C.; he will get her a secretarial job with his company. When Whitley insists on attending summer school and taking an internship, Julian accuses her of being sheltered. Whitley goes to Dwayne's apartment in search of advice, and mistakes Mrs. Wayne for a maid. Dwayne tries to cheer Whitley during a dinner party organized by his mother; he admits that Whitley is spoiled, but believes that Julian should give her some credit for setting her sights on a career. Mrs. Wayne warns her son that Whitley is trouble. Whitley gives Dwayne a gift and thanks him for always being so supportive. Mrs. Wayne asks her to join them at Dwayne's induction ceremony.

Dwayne falls apart in the aftermath of his kiss with Whitley. He cannot sleep due to recurring nightmares, and lets the apartment turn into a pig pen. Kinu becomes extremely bossy and territorial; she argues with Ron (who is tired of her constant presence at the apartment), then tries to bar Whitley from a party honoring Dwayne's and her six-month anniversary. Ron, hoping to drive Kinu over the edge, hires cash-poor Whitley as a housekeeper. Dwayne's mother arrives in the midst of the women's sniping because she had sensed that something was wrong with her ""chipmunk."" Mrs. Wayne doesn't like Kinu any more than she does Whitley, so Whitley tries to take advantage of the situation by buttering her up. Kinu finally snaps and takes it upon herself to fire Whitley. Dwayne admits to Kinu that he cannot shake his feelings for Whitley. They decide to break up.

Dwayne takes Whitley and Ron to his parents' house for Christmas. Whitley is desperate to impress Dwayne's mother. She sneaks out before dinner to buy an expensive present for Mrs. Wayne. After she misses the subway, a panhandler dressed as Santa Claus accosts her and steals the gift. Whitley stops the thief with some help from the police, but the gift is broken. Mrs. Wayne apologizes for giving Whitley a rough time and urges her not to try so hard. Ron's father punishes him for refusing to work at the dealership by cutting him out of the family's Hawaiian vacation. Ron seeks solace by stuffing his face with Mrs. Wayne's cooking until his father offers him a reprieve.

Before Dwayne and Whitley can deal with the repercussions of his revelation, her mother arrives for the engagement party. Dwayne's parents come to town, and Adele and Marion instantly despise each other. They clash over preparations for the party and wedding, and end up getting into a scuffle and throwing flowers all over the dorm lounge. Dwayne tells Whitley that he is feeling trapped; he fears that they are rushing into marriage. Dwayne has a talk with his father, who insists that it is common to have cold feet. Mrs. Gilbert and Mrs. Wayne establish an uneasy truce during the party. Each of the parents makes a touching toast to the couple and its future. Whitley announces that she is calling off the wedding and runs out. Dwayne follows her and pleads that he still loves her. He points out that his father said that everyone has doubts. ""Doubts, Dwayne. Not dates,"" she replies. Whitley tells Dwayne that she wants to be with him for the rest of her life, and asks if he can say the same.

Whitley's mother surprises Whitley and Dwayne by coming to visit for Thanksgiving. Whitley is too ashamed to admit that she is unemployed and that the couple was recently robbed. Marion stuns Whitley by introducing her fiancé, Malik, a much younger man who sells oils and poetry for a living. Although Dwayne believes that Whitley should let her mother live her own life, she fears that Malik is a golddigger. She asks Kim to come over and flirt with Malik in the hopes of driving the couple apart. Just when it seems that things can't get any worse, Dwayne's mother (who has not spoken to him since he married Whitley) shows up on the Waynes' doorstep. Freddie tries to avoid Ron and re-commit to her relationship with Shazza. She even dons her old ""earthy"" look for a rally on behalf of Haitian refugees, but a law school assignment conflicts with the protest.

Marion and Adele clash over preparations for Thanksgiving dinner and throw food all over the kitchen. Marion takes Malik to task for paying too much attention to Kim. However, he is not her fiancé, but rather an actor whom she hired to break up Dwayne and Whitley. Malik backs out of the deal and joins the rally for the Haitians. Adele and Marion are mistaken for protesters and hauled into jail. When they wonder why they haven't been bailed out, Freddie breaks the news that Dwayne and Whitley are broke. Adele and Marion seem to bond over their disdain for their children's marriage. After returning to the house, Adele admits to Dwayne that she is mostly upset because she didn't get to see his wedding. Whitley assures her mother that she is happy, and everyone makes up. Shazza tells Freddie that he is aware of her dalliances with Ron. She admits that she can't decide which man she wants, so they end the relationship.

Whitley discovers she's pregnant; Dwayne's computer-baseball game is a hit with Kinishewa Corp., which wants him to move to Tokyo.

Marion and Adele's interference causes tension between Dwayne and Whitley; Ron considers suing Dwayne.