Never Been Kissed Synopsis: A newspaper reporter enrolls in high school as part of research for a story.
Josie is a junior copywriter at the Chicago Sun-Times newspaper and desperate for a chance to become a real reporter. That chance is given when her editor-in-chief gives her a story that requires her to go undercover as a high school student to expose what teenagers are into and up to. Socially awkward, Josie doesn’t fare very well in the beginning, becoming friends with the “nerds” rather than the popular crowd. But then her older brother Rob decides to help her by posing as a teenager as well, and his popularity helps catapult Josie into the cool crowd.
When Never Been Kissed came out in 1999, it was cute as hell. Drew Barrymore was at her peak adorkableness and anyone who had a rough go of it in high school could probably relate to Josie’s plight. High school bullying sticks with a person! There’s a reason most people say no thank you to the idea of returning to high school.
David Arquette, Molly Shannon, and John C. Reilly do an excellent job rounding out the cast, bringing their own brand of comedy to the movie. The high school students were fine, though the popular crowd was portrayed as your typical one-dimension bobbleheads. Leelee Sobieski is their foil – a serious, intelligent student who befriends Josie when everyone else gives her grief. Watching this, I remembered that I was not a huge fan of Sobieski when her film career was taking off. She was very bland in Never Been Kissed, and I can’t say I was sad when her character’s screen time dropped.
But let’s discuss the felony in the room! I admit that in 1999, I didn’t think much about the romance between Josie and her English teacher, Sam. Because I knew she was an adult and he was cute, if not the strongest actor. Even now, I really love the ending, with Josie waiting for Sam on the baseball pitch to get her first kiss. You know he’s going to show up, but the waiting is still rough!
But as an adult, it is quite a bit cringey. Sam is an adult attracted to Josie, who he thinks is seventeen. We know she’s lying, but he doesn’t. So it does make some of their interactions more creepy than romantic. I know many romantic comedies from the past have not aged well, but I can do my best to look at them through the lens of the time in which they were made. Some are just easier than others.
That being said, I enjoy Never Been Kissed more from the perspective of Josie’s journey from awkwardness and timidity to embracing her strengths and becoming more confident. Barrymore gives us a relatable heroine for whom we can root. She’s honestly the most authentic character within that high school, which is a shame because it would have been nice to see teenagers who aren’t stock characters of every other teen comedy out there. But… take the romantic angle out of it, and it’s a really cute movie.
Watched: 03/08/2023
Notable Song: Don’t Worry Baby by The Beach Boys
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