Drive Me Crazy (1999): Prom

April 7, 2025

It’s prom season. I am long past that season of my life, but I love a movie that takes me back to a more carefree and rose-colored time, look no further than this late 90’s rom-com with teen queen Melissa Joan Hart. While the movie is not technically set during prom, the “Centennial Dance” is a pretty decent stand-in.

Nicole, a type-A social organizer who has her prom vision perfectly mapped out, until her ideal date falls through. Desperate not to show up alone, she convinces her next-door neighbor Chase to pretend to be her boyfriend. You know what happens next, but it is still full of fun, butterflies, and high school drama.

What makes Drive Me Crazy the perfect prom-prep watch isn’t just the classic friends-to-enemies-to-lovers trope or the alt-rock soundtrack. It’s the way the movie captures that prom night energy: the expectation that something big is going to happen, the mix of nerves and excitement, and the slow realization that the person you really want might have been there all along..

If you’re getting your nails done, doing your makeup, or just daydreaming about the big night, Drive Me Crazy is a nostalgic, feel-good film that will get you in the mood for prom. I definitely recommend adding this to your prom night watchlist.

Available on: Prime Video

Holiday rating: 7 limos