The Many Loves of Dobie Gillis (1959)

S3E9 The Second Most Beautiful Girl in the World

Title: The Second Most Beautiful Girl in the World Plot: Dobie discovers that his charming new girlfriend, who has a kind spirit, is also being pursued by another boy during their outings together. Each time they go on a date, he realizes he must compete for her attention, leading to a series of humorous and awkward situations as he navigates this unexpected love triangle.