Never Been Kissed (1999)

Never Been Kissed is one of those rom-coms that works less because it’s plausible and more because Drew Barrymore makes you want to root for the person at its center—she plays Josie with such bright, wounded sweetness that even the movie’s contrivances start to feel like part of the fairy tale. The vibe is pure late-’90s comfort: funny, a little cringe in that high-school-flashback way, and surprisingly tender about how old humiliations can cling to you long after graduation. David Arquette adds a loose, good-natured counterbalance, and the film keeps things breezy even as it dips into earnest, wish-fulfillment romance. It’s not for everyone—some viewers will be understandably put off by the teacher-student setup and the undercover premise—but if you can accept its heightened sitcom logic, it’s a warm, crowd-pleasing watch with a big, hopeful heart.

Never Been Kissed wants to be a sweet, wish-fulfillment rom-com about rewriting your teenage misery with a second chance, and Drew Barrymore’s earnest charm does a lot of heavy lifting. The problem is the premise is so contrived and the script so thin that you’ll feel the plot bending itself into shape scene by scene, with logic gaps big enough to distract even casual viewers. More importantly, the central romance leans into a teacher-student dynamic (even if it’s undercover) that can feel ethically squirmy rather than swoony, depending on your tolerance. If you can accept late-’90s sitcom silliness, broad comedy, and a fluffy fantasy over realism, it’s an easy watch; if you need believable stakes and clean moral footing, this one may grate fast.