When a mature-looking young woman named Victoria Diamond approaches the Mr. Dennis Escort Service seeking an escort to a party, Roger thinks that escorting her will be a good chance for Winston to prove he can make it in the escort service business. But Victoria insists that Roger escort her, and when Roger arrives with her at the party, he discovers that she is only 16 years old, that it is her sweet sixteen party, and that she is using him to make her boyfriend Cliff jealous.

A woman hires Roger as her escort and cons him into pretending to be her husband on a television game show.