Never Been Kissed (1999)

In the delightful 1999 romantic comedy *Never Been Kissed*, audiences are introduced to Josie Geller (Drew Barrymore), a baby-faced junior copywriter at the Chicago Sun-Times. Desperate for a groundbreaking story, Josie is tasked with posing as a student at her former high school to research contemporary teenage culture. With the help of her quick-witted brother, Rob (David Arquette), Josie navigates the treacherous social landscape, infiltrating the inner circle of the most popular clique on campus. However, her meticulously planned investigation hits a major snag – and her own failed love life comes into sharp focus – when she unexpectedly falls for her dreamy English teacher, Sam Coulson (Michael Vartan). *Never Been Kissed* earns its place on any "Best Romance Movies" list by masterfully weaving together humor, heart, and a deeply resonant message about self-acceptance and finding love on your own terms. The film expertly portrays Josie’s transformative journey from an insecure, unkissed adult haunted by her past to a confident woman who finally experiences genuine connection. The undeniable chemistry between Drew Barrymore and Michael Vartan elevates their unconventional romance, culminating in one of cinema’s most iconic and satisfying declarations of love on a baseball field. It's a heartwarming testament to second chances and the idea that true love isn't just about a first kiss, but about finding someone who sees and loves you for who you truly are, awkward past and all.