Never Been Kissed (1999)

In this charming blend of romance, comedy, and drama, we follow Josie Geller, an endearing yet awkward junior copywriter at the Chicago Sun-Times. Tasked with posing as a high school student to delve into the complexities of modern teenage life, she finds herself navigating the treacherous waters of cliques, crushes, and the ever-elusive quest for acceptance. With her brother Rob lending a hand, Josie infiltrates the popular crowd, only to discover that her greatest challenge isn't just fitting in—it's confronting the romantic feelings that blossom for her captivating English teacher, Sam Coulson. What makes this film truly special is its exploration of themes like self-discovery, the trials of adolescence, and the timeless quest for love. As Josie balances her undercover mission with her own insecurities and the echoes of her past, viewers are treated to a heartfelt and comedic journey filled with relatable moments and genuine emotion. With a winning performance by Drew Barrymore, this film reminds us that sometimes, the most profound connections appear when we least expect them. It's a delightful reminder that some things—like true love—are indeed worth waiting for.