Josie Grossie In Never Been Kissed Would Be The Cool Girl In 2026

The ‘90s and early 2000s were a beacon of great rom-com films. While they all seemed to follow the same kind of premise — girl gets a makeover and becomes “hot” by taking off her glasses, girl is dumped by the cute guy and falls in love with the weirdo, girl has a mortal enemy in a boy she eventually dates, etcetera — one of them always stood out to me. Because in 1999, Drew Barrymore starred in Never Been Kissed, and literally, I was never the same again.

And not just because that movie introduced me to Michael Vartan.

Like other ‘90s and early 2000s movies, Never Been Kissed has been seen as problematic in recent rewatches. But 25 years after this movie was released, I’m more focused on Barrymore’s character of Josie Geller... and how, honestly, she was ahead of her time.

Of course, we’re supposed to see Josie Grossie — an unfortunate nickname bestowed upon her in high school — as a big, giant loser who has nothing going for her. She’s dorky, she lacks social skills, she’s smart. You know, all the attributes every movie gave every bullied character. But as she becomes a young adult, Josie still holds onto those parts of her life, and she never seems ashamed of them. From creating another cross-stitch pillow to adorn her bed to correcting her colleagues when they mess up the English language, Josie Geller is always true to herself.

And, in 2026 trends, she would’ve been cool as hell.

Imagine, for one moment, Josie Geller with a TikTok. Her “get ready with me” videos would include her dressing in some pretty incredible outfits — whether she’s being the high school version of herself or the adult version of herself — all while sharing tidbits about Shakespeare and calculus. She could do voiceovers about how much she was bullied (never has my heart broken so much in a movie as her mom calling out for her when she’s been egged by her prom date) while showing you her latest granny hobby. She absolutely has an analog bag full of books and writing materials, while also being a badass career woman who owns her own house in the Chicago suburbs at age 25.

Josie Geller was supposed to be a loser in Never Been Kissed. And sure, she gets her redemption arc after she changes her hair and starts wearing more flattering clothes (the way I coveted that pink dress on the baseball mound), but the core of her character is an absolute vibe. Especially with the old lady tendencies.

She’s the cool girl who understands how sex actually works, and a girl who knows that she should only put her energy into a real, true love. She’s the girl who isn’t afraid to jump into something new and scary, even though that kind of trust and confidence hasn’t worked in her favor in the past. She’s the girl who would use her TikTok lives to talk about injustice in the world, all while getting super excited about some new lipstick she bought and the embroidery she’s working on.

1999 Josie Geller was a dork. But in 2026? She would be an absolute icon.