Does ‘Never Been Kissed’ Hold Up Today? Spoiler Alert, Not at All

When Josie Grossie stood on the pitcher’s mound in hopes of having her first kiss, viewers everywhere swooned — but how well has Never Been Kissed aged more than two decades later?

The film, which hit theaters in 1999, follows Josie Gellar (played by a 20-something Drew Barrymore), the youngest copy editor at The Chicago Sun-Times with grand hopes of one day becoming a full-time reporter. When her publisher (Gary Marshall, in his most cartoonish role yet) assigns her an investigative feature in hopes to uncover what’s really going on with teenagers in the ‘90s, Josie jumps at the chance to relive her high school experience.

Once Josie hits the hallways, though, she has a crucial awakening: high school was a nightmare. But one makeover later and a request from her also fully grown brother, Rob (David Arquette), to join her, Josie’s luck begins to turn around. Not only is she coming back with hard-hitting news that’s impressing her boss, she also meets her English teacher, Mr. Coulson (Michael Vartan), and sparks fly.

While the film is undoubtedly a classic ‘90s romp full of humor and heart and an always endearing Barrymore, the outrageousness of the premise can’t, and shouldn’t, be ignored. From adults masquerading as — and dating — teenagers to a teacher who thinks falling for a 17-year-old child might be OK, Never Been Kissed misses the mark.

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Despite its shortcomings, Barrymore herself looks back on the experience as a positive one. While resisting her time filming the movie, Barrymore told fans that Never Been Kissed was her first official movie at her production company, Flower Films, sharing that she wanted to make something based on a universal experience: growing up.

“It’s raw and ridiculous, beautiful and helps you decide what is important and what isn’t,” she wrote via Instagram. “But we also loved humor. And if pain isn’t mixed with insane laughter, then it doesn’t work,” she wrote via Instagram in April 2019. “Humor and humility are linked like besties! And everyone feels vulnerable while they are figuring out who they are and what they stand for. It also helps when you have the best cast and great music and everyone is making the same story! Josie Grossie forever.”

While Barrymore’s love for the film is appreciated by Us, there’s no denying it hasn’t aged well. Here’s every reason Never Been Kissed does not hold up today:

The Women Are 2 Dimensional

Despite the fact that this is a female-led cast, the women over the age of 18 in Never Been Kissed don’t ever feel real. While Molly Shannon’s Anita is hilarious, she is portrayed as utterly sex obsessed, from her willingness to get fired just to get a man’s attention to suggestively sucking on pencils in meetings for laughs. Josie, meanwhile, is the virgin of the film, which equates to knitting, correcting people’s grammar at every turn and spending her time alone at home with her turtle. Is there really no middle ground here?

The same goes for the teenagers. There’s a seriously impressive cast of “popular” mean girls — played by Jessica Alba, Marley Shelton and Jordan Ladd — but they’re barely given anything to do and have no real motivation for their cruelty. Leelee Sobieski’s Aldys, meanwhile, is solely focused on mathletes and erasing any and all school-sponsored events from existence.

The Girlfriend Is Horrible Because Of Course She Is

A tried and true pattern of the ‘90s, Mr. Coulson’s — or Sam, to those he isn’t teaching — girlfriend (Maya McLaughlin) is instantly horrible. Seconds after appearing on screen, she’s already complaining about the “smoke” and “noise” in the club, and waxing poetic about how the Met is the only valuable form of socialization, all at the old age of 25.

Sure, Josie is the protagonist here, but there’s no need to make the love interest so viscerally unlikeable.

Adults Hang Out With High Schoolers

For some reason the film fails to explain to Us, it’s very important that Josie go undercover into the world of high school. It’s a peculiar choice considering she could just interview teens instead. The ick-level only spikes when Josie’s boss is unsatisfied with her day-to-day activities, and instead demands that she uncover the “sex scandals” that are happening behind closed doors. Why adults need to be privy to the sex lives of 17-year-olds, remains a mystery.

… And Then ‘Truman Show’ Them Without Their Consent

If hanging out in the cafeteria at 30 isn’t bad enough, the newspaper orders Josie to secretly record her experience. What that boils down to is filming underage kids without their — or their parents’— consent, and then using their private information for public fodder.

It also means a man sits outside the school all day in an unmarked van cutting together footage. Stranger danger, kids.

A Grown Man Hooks Up With a Teenager and That’s OK, for Some Reason

Even older than Josie, Arquette’s Rob returns to high school — after being a popular jock the first time around — to help his sister and get another shot at a baseball career. It’s a problematic choice to begin with, but things take a turn for the worse when he begins dating a sophomore in high school. It’s been a while since we graduated, but that equates to something around 16 years old, max, right?

When Josie reminds him of the fact, he responds, “I know! And a gymnast.” Yikes! (Don’t forget one of Rob’s first lines in the film: “We’ve got some underage hotties this year!” after seeing photos of Josie’s “classmates.”)

Josie also accepts an invitation to the dance from Guy (Jeremy Jordan), the most popular teen in town. The two never actually hook up, and it’s mostly for Josie to get a chance to relive her disastrous prom experience, but still not a good look.

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A Teacher Falls for Someone He Thinks Is a Child

While so much of Never Been Kissed is about Josie learning to love herself, the romance between her and Sam, the English teacher, is also a main plot point. And while no, Josie isn’t really a 17-year-old high school student, Sam thinks she is and continues to flirt with her anyway.

After joining Josie on a romantic Ferris wheel ride (already a red flag), he opens up to her about his relationship problems (also extremely inappropriate). After telling her that when she’s his age, she’ll have “guys lining up around the block” to date her, he proceeds to ask her to the dance. Again, this man thinks he’s talking to someone who is 17. We can’t stress this enough.

The twosome also share a dance at the masquerade ball, in front of the whole school, and this is also found to be acceptable by everyone else in attendance.

The End Doesn’t Quite Make Sense, Even If It’s Sweet

One would think that once Sam finds out that he isn’t in love with his underage student, he’d be happy. Except he’s not; he’s furious, actually, and storms off threatening to move to New York City with his terrible-I-hate-everything girlfriend. Rob also blames Josie (even though he’s the one who volunteered to join her) because now he can’t play in the school’s championship baseball game as a 30-year-old, Josie has no story and she’s fired from The Chicago Sun-Times (which is weird, because wasn’t she just following her bosses orders?).

In an effort to win back her one true love, Josie writes a piece for a rival paper, confessing her entire scheme. She shares that she will stand on the pitcher’s mound before the game starts waiting to have her first real kiss with Sam, who she hopes will forgive her.

Why Josie and Rob are not in more trouble over their scheme is unimportant, apparently, but there is vague explanation that the school, the paper and everyone involved will somehow benefit from this public display of affection.

Of course, everyone Josie lied to eventually forgives her for her wrongs, and they show up to cheer her on. With seconds left on the clock, Sam appears and two share a kiss before riding off into the sunset.

It’s a happy ending, we’re just not sure how we got here.