Season 5
| Episode 10 -
Misleading Lady
Synclaire auditions for a role in a prominent comedy troupe, whose alumni include Whoopi Goldberg and a guy from Good Times. Although her audition is extremely impressive, she learns that all the spots for women have been filled. Synclaire disguises herself as a man and assumes the role of James ""Jimmy"" Overton. She wins the part and (thanks to coaching from Overton) consistently fools the cast and crew. However, Overton is distressed by the fact that the couple cannot show affection in public, particularly after hearing that Jimmy may have a long and prosperous career ahead of him. Unable to accept the strain her charade is putting on her marriage, Synclaire reveals her true identity during an improv sketch. After helping Tripp out of a jam, Khadijah begins to believe that she has what it takes to be a big-time jingle writer--much to Tripp's annoyance.