Never Been Kissed: Things Only Adults Notice In The '90s Rom-Com Classic

Never Been Kissed is a movie almost as iconic to the year 1999 as Britney Spears' "...Baby One More Time" Billboard Hot 100 debut and the release of J.K.Rowling's the third Harry Potter book, at least among '90s kids. When a star called Drew Barrymore bagged the lead role in Never Been Kissed, it quickly became a beloved movie that's now ranked within the top '90s classics. 

It also remains one of the first titles we think of when listing Barrymore's films. The times, however, have changed since then, and society is much more woke. For this reason, revisiting some of our favorite classics can be fun, but it can also be very eye-opening. That means that when we re-watch this movie as adults, we're spotting so many moments that totally passed us by the first time around. Moments that make us get our side-eye on and ask, really?! 

So, if the first image that springs to mind when reflecting on Never Been Kissed is that of a made-over Josie Grossie standing in the middle of a baseball pitch waiting for her dream guy to run down the stairwell and sweep her off her feet, please accept our apologies now. The following points are probably going to ruin that happily ever after for you because, while this movie will remain a favorite for nostalgia's sake, it does not age well.

Let's kick this off with some real talk: There is no way on earth that Drew Barrymore's Josie Geller — a 25-year-old professional woman — could pass as a 17-year-old high school student. While we can confidently assume that Josie didn't spend her early 20s with her head in a keg, guzzling beer and chain-smoking the years away, that eight year age gap would still leave telltale signs. 

But nobody in this high school really seems to notice (apart from Michael Vartan's Sam Coulson, but more on him later) — we didn't even really notice when watching Never Been Kissed the first time around — and that is really hard to believe.

Okay, so Josie is out of touch with all things "cool" — she always has been. Do the math: If she's now 25 years old and joining the class of 1999, then her real prom would have been in the early '90s. Yet in every flashback of her as a teenager she's wearing extremely '80s clothes, which is either a mistake in the film's timeline or a way of showing just how out of touch she was. 

And this doesn't really change when she goes back to high school — her outfit has been picked out by an older colleague (Anita, played by Molly Shannon), and it makes her stick out like a sore thumb. A bouffant and white feather boa to high school? In the '90s? Subtle, Josie. 

On to Mr. Sam Coulson, Josie's English teacher who was 100 percent swoon-worthy back in the late '90s. Some decades later however, not so much. In fact, watching Mr. Coulson's behavior in Never Been Kissed makes us want to reach for the nearest red flag and wave it about wildly because seriously... this guy.  

In his first class with Josie he asks her "are you sure you're 17?" — the only person who questions her age — indicating that he somehow gets her on a deeper level and can see through her. She insists that she is, the conversation moves on, and he continues to flirt with her throughout the rest of the movie. We're talking longing looks, ferris wheel rides (in which he tells her that "guys will be lined up around the block" when she gets a little older, then acknowledges how inappropriate that statement is), and messing around with paint. Pretty borderline, right? It gets worse.

When Josie outs herself as an undercover reporter, Sam's pretty mad and tells her he just can't look at her the same way. You mean, you can't look at her in the same way because she's legal, Sam? Is that what you mean?

All this before we even get onto the point that he's in a long term relationship and supposed to be relocating to NYC imminently to be with his girlfriend. Yes, she seems overbearing and like she doesn't quite "get him," but that's beside the point. 

On the topic of matters that aren't technically legal, how well would an undercover reporter with a secret camera pinned to her chest filming in a high school go down in a court of law? If we had to stagger a guess, we'd say probably not very well. 

Then add in the fact that there's a dude in a van parked outside the school watching the live footage, and a bunch of middle aged folk crowded around a screen, streaming it in their office. Can you imagine how much trouble the newspaper would get in if this actually happened? You can almost picture the headlines now: "Reporter Infiltrates High School, Films Teenage Girls!" How were we not even mildly disturbed by this before?

Rules around filming in high schools differ from state to state, so perhaps they wouldn't all be slammed in jail immediately, but it seems pretty clear that the minimum you need to film in a public school is permission from the board. And considering how shook everyone was — teachers included — when Josie reveals her true identity in front of the school, something tells us that the permission wasn't granted or even requested.

 Not a great start for someone trying to advance their professional career. At Never Been Kissed's version of the Chicago Sun Times though, nobody seems that bothered with such a minor detail.

Then we get to Rob Geller (David Arquette), Josie's brother, who gifts us — the now adult audience — with quite the conundrum. On a mission to make his sister's life more bearable, he too drags his 20-something butt back to high school (and also somehow manages to pass for a teenager despite having crow lines and 5 o'clock shadow) with the aim of joining the soccer team and making Josie popular. 

Watching this back in the late '90s, we considered his move quite sweet — her figurative knight in shining armor, riding into school on the back of a giant bucket of "Kole Slaw" and spreading rumors about how she's actually a really "rufus" chick underneath the dorky persona. But watching as an adult? Not so sweet.

Most of the rumors Rob spreads are pretty harmless: Josie has a cool yacht in the South of France in which she spends her summers; Josie's the heir to her inventor father's fortune; she once dated and promptly dumped the drummer from Big Bad Voodoo Daddy. 

But then he takes it too far — not only does he tell people that he dated her (very weird), but then specifies that they're still "really good friends," which he says in such an odd, nod-and-wink kind of way that kind of insinuates that they still hook up from time to time. Blech!

Even beyond the nausea-inducing brother-sister/former lovers heebie jeebies, thinking about it now, Rob's actually a bit of a jerk — a jerk who dabbles in some pretty shady behavior. 

First, if he cared so much about Josie's well-being and making her popular, why didn't he do this the first time around? He was moving with the "right" crowd back then, he already knew what it would take to get his sister out on top, so why didn't he employ those tactics when they were both actually in high school and save her the trauma of a savage prom egging from that jerk Billy?

Second, he uses his place of employment — the Tikki Post — to make a counterfeit I.D. card, which he then uses to enroll in high school with absolutely zero comeuppance. In fact, after Josie outs his real age and agenda at the prom, Rob's given a job as assistant coach on the baseball team. Crime is rewarded in this movie, guys!

Last, but certainly not least, he's dating a 16 year old. Sure, sometimes age ain't nothing but a number, but sometimes that number is giant, flashing warning sign that you should avoid at all costs, dude.

If you regularly re-watch the movies that made your childhood, no doubt you're accustomed to the practice of yelling "OMG, is that —- ?!," pausing the film and consulting its IMDb page immediately. That procedure is no different with Never Been Kissed.

While most people know that Jessica Alba starred as Kirsten, one of the three popular girls, we're willing to bet that you totally missed another (now very famous) face hiding in that gang. While you were busy swooning over Guy, one of his BFFs was totally overlooked. That BFF was Golden Globe award winning actor, James Franco. And what's more, it was his first feature film! Jeremy Jordan — the actor who played Guy — however, unfortunately hasn't had the same industry success, with only three credited roles since Never Been Kissed premiered in 1999.

Cooler still, this teen classic marks another early career appearance for one more industry great — one who won an Oscar for Best Supporting Actress in 2012 for The Help, and two further Academy Award nominations in the same category in 2017 and 2018 for Hidden Figures and The Shape of Water. Yes, you guessed it — Octavia Spencer is in this film, too!

While most of the entries on this list require you to look at the social context around narratives to consider them in a new light, this one should have been glaringly obvious right from the start. However, for some completely head-scratching reason, it wasn't obvious at all, despite being declared by Josie herself in the movie's early stages. You see, Josie has been kissed and thus the title Never Been Kissed is actually one big fat lie.

The reveal comes while Josie's chatting with Anita (Shannon) and Cynthia (Spencer) before she's even given the undercover assignment. Anita is asking Josie to go on a double date with her, when Josie says, "When I finally get kissed, I'll know," which promptly leaves Anita's eyebrows free to hit the ceiling and exclaim, "If you've never kissed a guy we have bigger problems," and us, the audience to root for her romantic endeavor. 

However, Josie responds, "I've kissed guys. I just haven't felt that thing." Hold the freakin' phone, Josie! You've kissed guys? What are we doing here then?

Unless you had quite the active childhood, the realism (or lack thereof) in the scene in which Josie gets completely mashed off her nut on hash brownies probably won't have been apparent to you until re-watching the movie with wiser eyes. 

To recap, in order to get "down with the kids," Josie attends a party at a Reggae club (an odd choice of venue for white, middle class teens, but whatever), devours a space cake gifted by some extremely stereotypical Rastafari (the problems in this scene are bountiful), and proceeds to transform into the most hyper stoned person the world has ever seen.

Call us jaded, but what kind of human chows down on such a cake and then suddenly gets such a fire-cracking surge of energy that she cops a pink feather boa — the second boa in this movie, may we add — off someone in the crowd and then gyrates upon it onstage in front of the very table of kids she's trying to win over? No kind of human, that's who. Not only does this scene embody the very definition of cringe (which also makes it great, obviously), but her behavior is just not realistic — like, at all. Then again, writers and directors seem to have a hard time with this in general.

If we take a moment to appreciate the coolest character in Never Been Kissed, LeeLee Sobieski's Aldys is truly deserving. So deserving that she should have landed her own sequel or spin off to be honest, or at the very least a little more recognition. But were we ready to give that to her as teenagers? Of course not. 

Most of us aspired to be the cool kids, a member of the gang everyone wanted to be part of, to hang with the our school's equivalent of the Gus and the Kirsten, despite the fact they were pretty awful people. Watching as adults, however, is a totally different ball game.

Aldys is real. She's super smart and wears her mathlete "The Denominators" jumper with pride, giving limited thought to whether that makes her lame or not. She's loyal, and expects her friends to be loyal, hence the shade she throws at Josie for ditching her at the cafe and for turning into a "lemming." 

She's interested in the world and she dreams of being a professor, an architect, a flutist, a novelist, a potter, a painter, and of going to Northwestern; she dreams of a life filled with culture and color, which is so much more than you could say for any of the other characters in this movie. And for that, Aldys should be praised.