"Doug Plays Cupid" is the Valentine’s Day episode of Dougin the Disney era. It first aired on May 22, 1999, on ABC.
Plot[]
Roger gets Doug to teach him how to be a gentleman in order to get Beebe to ask him to go to the Bumpkin Day Hoe-Down Dance with him where the girls ask the guys. Doug hopes Patti will ask him, but she's sick and Doug is afraid she'll ask someone else once she's better. Also, Skunky shows his friends that he has webbed toes, which is distracting everyone in gym class, so Coach Spitz forces Skunky to cover up his toes at all times. Not listening to Beebe, Roger throws a water balloon and makes Mr. Bone fall down with cake on him and angers him. Skunky confronts Coach Spitz and tells him not to force Skunky to cover up his toes. Roger tries to throw another water balloon and Doug and Patti, but Mr. Bone lets him have detention.