The "Ick" factor vs. 90s logic
If you’re revisiting this for the first time since the Clinton administration, the first thing that will hit you isn't the soundtrack or the tech—it’s the teacher. The central romance between Josie and Mr. Coulson is the definition of problematic. In 1999, we were supposed to find it swoony that a faculty member was falling for a student because, hey, she’s actually a 25-year-old reporter.
In 2026, your teen is going to have questions. The movie tries to bridge the gap by making the teacher a "sensitive soul" who thinks he’s found a literal kindred spirit, but the power dynamic remains a wreck. It’s best to treat this as a historical artifact. Use it to talk about why those boundaries exist in the real world, even if the "student" is secretly an adult. If you want to see how this stacks up against other high school milestones, check out our list of the 15 best prom movies ranked by age appropriateness.
The Drew Barrymore carry
There is a reason this movie holds a 69% audience score on Rotten Tomatoes despite a much lower critic rating. That reason is Drew Barrymore. She is doing heavy lifting here, pivoting from "Josie Grossie" flashbacks to the wide-eyed optimism of a woman getting a second chance at the one thing that traumatized her.
She makes the "undercover" trope work because she plays Josie as someone who never actually grew up emotionally after high school. While the plot is formulaic, her performance is genuinely vulnerable. When she shows up to a party in a white feathered marabou outfit or completely whiffs a cool-girl greeting, it’s painful in a way that anyone who felt like an outsider will recognize. It’s less a movie about journalism and more a movie about the scars we carry from being fourteen.
Why it still works for the "outsider" kid
If your kid is currently navigating the social meat-grinder of middle or high school, they might actually find this more relatable than the hyper-polished world of Euphoria. Never Been Kissed captures the specific, sweaty-palmed anxiety of trying too hard.
The movie is at its best when it focuses on the "Denominators" (the math nerds) and the idea that being "cool" is a temporary, mostly fraudulent state of being. It’s a quintessential entry in the genre, and if your family is on a kick of school-sanctioned social drama, it fits right into the classic prom movies you need to see.
The "Fast Times" comparison
Critics at the time, including those at Rolling Stone, noted that this movie feels like a sanitized, rom-com version of Fast Times at Ridgemont High. It swaps the grit for gloss. While it’s rated PG-13, the "edgy" elements—teen drinking, some light innuendo, and the mean-spiritedness of the popular clique—are fairly tame by modern standards.
The real friction isn't the content; it’s the pacing. Like many comedies from this era, it meanders. If your teen is used to the rapid-fire editing of TikTok or modern streamers, the first act might feel slow. But if you can get them past the setup, the payoff on the baseball mound is the kind of big, cinematic cheese that only the 90s could truly pull off. Just be ready to explain what a "copy boy" is.
