Peak ’90s Nostalgia With a Problematic Core: Never Been Kissed

Never Been Kissed is unmistakably a product of the late 1990s. From its fashion to its pop soundtrack to its premise, it belongs to a pre-9/11, pre-social media era when the idea of an adult reporter casually enrolling in a high school felt whimsical rather than alarming. Given how secure schools are today, this story simply could not happen now. The concept is spiritually inspired by Cameron Crowe’s real-life return to high school as a reporter for Rolling Stone, which later became the basis for Fast Times at Ridgemont High. But where Crowe’s story leaned observational, Never Been Kissed leans romantic and fantastical.

The film explores themes of second chances, identity and reinvention. Josie Geller gets the opportunity to rewrite the most painful chapter of her life: adolescence. High school is framed as both a battlefield and a laboratory for identity, a place where popularity feels like survival and humiliation feels permanent. The movie also touches on the shallowness of social hierarchy, showing how fragile and performative popularity truly is.

At its best, the film understands the trauma of adolescence. The nickname “Josie Grossie” lingers over her adult life like unfinished business. Her second trip through high school is less about journalism and more about healing. There is something universally relatable in wanting to confront your younger self and do it differently.

Drew Barrymore anchors the film with charm and vulnerability. She moves convincingly between awkward, braces-wearing Josie Grossie and the more confident, socially adept version of herself. Barrymore plays both extremes with warmth, making Josie’s longing for acceptance feel sincere rather than pathetic. She carries the emotional weight of the film even when the material falters.

Unfortunately, the supporting performances are uneven. David Arquette, nearly 30 at the time of release, is not remotely believable as a high school student, which undercuts several comedic beats. Molly Shannon plays her role broadly and somewhat one-note. John C. Reilly is reliable as always, but the script does not give him much depth to explore. The most significant arc belongs to Michael Vartan’s English teacher, yet that storyline is precisely where the film ages the worst.

The writing is ultimately the biggest culprit in holding the film back. A teacher developing romantic feelings for someone he believes to be his underage student is uncomfortable by modern standards, and the resolution does not fully absolve the ethical concerns. Add to that jokes about statutory rape and newsroom employees catcalling teenage girls through Josie’s hidden camera feed, and it becomes clear how differently this material plays today. What was framed as edgy or humorous in the ’90s now feels tone-deaf and unsettling.

And yet, despite these issues, the film retains a certain endearing quality. Its message that popularity is fleeting and often hollow can be empowering for those who never fit in. At the same time, it suggests that confidence and authenticity, when genuine, can open doors. The climactic moment at the baseball field remains sweet in its optimism, even if the road getting there is flawed.

Never Been Kissed is a charming but dated romantic comedy. It captures the insecurities of adolescence with heart, even if its questionable plot mechanics prevent it from aging as gracefully as its star.