Ask Any Girl (1959)

Meg, an optimistic young woman, navigates a series of misfortunes in her quest for love in bustling New York City. After a suitcase mishap at Penn Station, a falling out with her roommate, and an awkward encounter with a lecherous boss, she seeks employment at a Manhattan motivational research firm. Here, she encounters the meticulous Miles Doughton and his charming, carefree brother, Evan. Amidst the chaos of her life, Meg's journey reveals unexpected challenges and potential romance in the vibrant city landscape.