My Three Sons (1960)

S6E25 Robbie's Double Life

Robbie enjoys the thrill of juggling two relationships at once—one with a high school girl and the other with a college student. However, when the two girls unexpectedly compare their experiences, they decide to take matters into their own hands. They conspire to confront Robbie by arranging for him to take both of them out on the same night, setting the stage for a comical showdown.