What Do We Do With Never Been Kissed, 20 Years Later?

It’s been 20 years since Josie Geller (Drew Barrymore) first stood on that pitcher’s mound at the big State Championship game, waiting for the man who, mere days ago, thought himself her high school teacher, to come and give her her first-ever kiss.

In hindsight, Never Been Kissed should always have been considered problematic. It’s a film about adults posing as high schoolers, framing inappropriate and predatory relationships either in the rosy glow of fantasy romance, or playing them for laughs. In light of our collective cultural reckoning post-MeToo, that premise has only gotten more fraught, standing as the perfect example of the banalization of pernicious behavior, and perpetuating the too-ingrained idea that it’s all in good fun.

But it’s also a classic of the teen movie genre, one that’s still frankly a delight to watch, largely because of Drew Barrymore’s charming and poignant portrayal of a woman on the ultimate journey towards self-acceptance. So, what do we do with Never Been Kissed?

As a young woman growing up in the early aughts, Raja Gosnell’s film, from a script by Abby Kohn and Marc Silverstein, was the sleepover standard. I must have seen it a thousand times, and to this day, Barrymore’s delivery of “Why her?” when Josie defends Aldys (Leelee Sobieski) from the same kind of cruel prom prank that left her scarred, is seared into my brain, a call to arms for any misfit teenage girl.

At 25, Josie Geller is the youngest copy editor at The Chicago Sun-Times. She dreams of being a reporter. So, when the paper’s curmudgeonly publisher (Garry Marshall) assigns her a huge investigative feature requiring her to go undercover as a senior in high school, it seems like she might finally be on her way. That is, until she remembers that her own high school experience was a nightmare hellscape. Could this be a chance at a do-over?

Rewatching the movie as an adult on the eve of the twentieth anniversary, I was struck by how much of it still holds up. Never Been Kissed speaks surprisingly eloquently to the traumatic experience that high school can be for teenage girls, constantly bombarded with conflicting messaging about where their value lies. For many, it’s an experience that resonates well into adulthood. Thus, the plot point about Josie never having been kissed. That plot point isn’t bad in and of itself. It would make sense that after being publicly humiliated by high school crush Billy Prince (Denny Kirkwood), Josie would have trouble trusting men. But the film wades into murky waters when it introduces English teacher Sam Coulson (Michael Vartan), he of the sexy bedroom eyes and a passion for Shakespeare, as the solution to that fear of intimacy.

Never Been Kissed didn’t invent the onscreen teacher-student romance. Nor did it bury it. It’s a trope that’s largely gone unchecked, showing up again and again in otherwise beloved pop culture phenomena. Dawson’s Creek, Pretty Little Liars, Ray Donovan, The O.C., Gilmore Girls, Friends, Gossip Girl, Saved By The Bell — all examples of shows that have featured this trope, either as a central plot point (Ezra and Aria on PLL), or as a short-lived fling (Ross and Elizabeth on Friends). As for movies, it’s almost impossible to count.

What’s interesting about Never Been Kissed is that it’s simultaneously self-aware that Mr. Coulson’s behavior is wrong, even as it glosses it over during the big finale. After reviewing the footage from Josie’s hidden camera, Josie’s editor Gus (John C. Reilly) — who, ironically, ends up in an interoffice relationship with his subordinate — tells her that this is the story: An adult teacher using As You Like it to flirt with a student he believes to be 17 years old. His indignant storm-out after she outs herself as a reporter in her twenties made me laugh out loud this time around. How can he be upset? This guy just found out that the girl he was developing feelings for is actually age-appropriate. If anything, he should be celebrating. (“What, you were hoping I’d be happy?” he says. “Because all of a sudden I’d be allowed to be attracted to you?” Dude. Yes!)

It doesn’t matter that he never made a move. He thought she was his underage student, and he still chose to have touchy-feely conversations about his love life with her on a Ferris Wheel, not to mention partaking in the time-honored romantic tradition of dabbing your partner’s nose with a paintbrush during a getting-the-gym-ready-for-prom-montage. He comments on her appearance, he wonders at her intelligence in a way that feels like he’s about to throw down on the desk in the middle of English class — he does all the small things that have, over the years, been coded to mean that a man is attracted to a woman.

But that’s arguably not even the most problematic part of Never Been Kissed. Even worse, in my opinion, is Rob’s (David Arquette) foray into high school to help his sister, and get a second chance at a baseball career. He is in full possession of the facts when he starts dating a sophomore. Worse, he’s into it. When Josie reminds him that she’s only 16, he responds “I know! And a gymnast.” Yuck. (For that matter, Josie’s accepting to go to prom with Guy Perkins, played by Jeremy Jordans, also skirts the line. They never hook up, but again, that’s not the point.)

The movie also portrays a woman’s identity as existing on one of two sides of an extreme spectrum. On one end, you have sex-crazed Anita (Molly Shannon), and on the other, virgin spinster Josie, who’s idea of a wild night out is finishing yet another needle-point cushion. Who are these women? Can’t a woman have a hobby without being labeled a hopeless loser?

Still, despite knowing all of this, I’d be lying if I said I didn’t love rewatching this movie. It’s funny, awkward in all the right places, and full of genuine heart. The scenes of Josie confronting her past bullying and ensuing anxiety feel like direct precursors to moments in Bo Burnham’s Eighth Grade. Never Been Kissed is a comedy, but it never took Josie’s plight lightly. The film was Barrymore’s first producing credit, setting the stage for her to take on a much more prominent role behind the camera, one she holds on the majority of her projects to this day. It also marked both James Franco (who has since become problematic himself) and Jessica Alba’s film debuts.

So many beloved classics require women to shelve a little piece of their brain in order to enjoy them today. New York Times critic Manohla Dargis wrote compellingly about this process in November of last year. But I’d argue that Never Been Kissed is an exception. It’s a film that’s very much a part of the next step of the public conversation about what kind of previously-tolerated gray area behaviors should now be revisited as flatly wrong. Last week’s Joe Biden news cycle proves that we’re far from having a definitive answer to that question. It’s going to take work, and that means grappling with deeply ingrained societal norms, tropes, and stereotypes — especially when they show up in our most prized pieces of entertainment.

Never Been Kissed isn’t going anywhere. To ignore its cultural impact is to repress an unpleasant memory in the hopes that it might just work itself out. Just ask Josie how that went.

Never Been Kissed is available to stream on HBO Now, YouTube, Amazon Prime, Vudu, Google Play, and iTunes.