Dwayne offers to tutor Denise in calculus after she receives a D on a test. Denise believes that it is a scam, but Dwayne turns out to be an excellent tutor. They study for so long that Dwayne gets locked inside the dorm after curfew. He sneaks into Whitley's room while she is sleeping and climbs out the window. Stevie catches Dwayne coming down the fire escape, and Whitley suffers tremendous damage to her reputation. Dwayne refuses to tell the truth because he fears that Denise could be suspended. Stevie believes that Dwayne and Whitley are lying, and plans to report them to the dean. Denise interrupts and explains what really happened.

Dwayne annoys a graduate student with his stupid pick-up lines. She predicts that Dwayne would freak out if a woman actually responded to his advances, and decides to invite him to her apartment. Jaleesa takes bets from the entire dorm on Dwayne's possible reaction. Denise feels that Dwayne does not deserve this treatment, and warns him that he is being set up. Ron persuades Dwayne to go to Peggy's apartment and win her over with his charm. Denise and Walter (Dwayne's resident director and P.E. teacher) try to convince Dwayne to be himself around women. Peggy realizes that Dwayne is a good guy and cannot follow through with the bet.

Whitley enters the Miss Hillman pageant in order to win the approval of her mother, a former pageant winner whom Whitley can never seem to please. Denise decides to fight the elitism of the pageant by convincing Dwayne to enter. The Gilbert Hall residents infuriate Whitley by backing Dwayne as their representantive in Miss Hillman. A fraternity sponsors Whitley; its members, along with other students, constantly mock Dwayne and play cruel pranks on him. Ron and Walter encourage him to save face by dropping out of the pageant. Dwayne refuses, and declares that the harassment he has received has prompted him to reconsider the way he treats women. Although Whitley receives more votes than Dwayne, she loses badly to another girl. Lettie and Denise recognize her disappointment and urge her to live her own life, without worrying about her mother's opinion.