The Monkees (1966)

S1E13 One Man Shy

Shy Peter finds himself smitten with the enchanting debutante Valerie Cartwright (Lisa James), yet he must navigate the challenges posed by her arrogant boyfriend, Ronnie Farnsworth (George Furth). As Peter attempts to capture Valerie's affection, he grapples with his insecurities and the obstacles that Ronnie presents, leading to a series of humorous and heartfelt encounters.