Shirley secretly takes a job as an advice columnist for the newspaper. Her first advice column unknowingly causes Dwayne's girlfriend to break up with him.
Maurice worries that he will be fired after he accidentally rips a hat donated by the famous singer Sharona for Nadine's charity auction. So he gets Darryl to help him sneak into Sharona's room to get another hat.
By running for class president, Maurice is able to win the affections of an attractive girl. However, she begins to manage his campaign and convinces him that his friendship with Darryl will hurt his chances of being elected.
When her dad comes into town, Shirley begins to experience the same feelings of neglect and disappointment that have plagued their strained relationship throughout the years.
Dwayne is reluctant to carry on a relationship with an older woman when Raj convinces him to not be concerned about age. However, Raj's feelings change when he and Nadine spot Dwayne out dining with an elderly woman.
Dee falls in love with Maurice's cousin, Reggie, a wheelchair-bound comedian, and has plans to join him on tour. However, Reggie has different plans, and tells Raj that he's going to hit the road without Dee and without telling her.
Nadine sets out to prove her suspicions that the exclusive club Raj is attempting to join discriminates against women, submitting her application and winning acceptance as a "man" after being rejected as herself.