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Never Been Kissed is a 1999 Romantic Comedy film starring Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon, and John C. Reilly, directed by Raja Gosnell, and produced by Barrymore's production company Flower Films. This is also one of the first movies of Jessica Alba and James Franco as part of the popular kid posse.

Josie Geller (Barrymore) is a 25-year-old journalist assigned to report undercover as a high school student to help parents become more aware of their children's lives. Back when she really was a high school student, Josie was a nerd with bad personal hygiene; as a result she was very unpopular. Her initial efforts to fit in at school are about as successful as they were in her teens, but with the help of her brother Rob (Arquette), Josie becomes more popular. She also finds herself falling for one of her teachers, who believes she's 17 years old and is disturbed by his own attraction to her. When he learns the truth, it becomes a question of whether he can forgive her for the deception or if that will keep them from being together.

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This film contains examples of the following tropes:

  • Acquired Situational Narcissism: Averted at first, but then play straight for a while later in the film.
  • Adults Dressed as Children: Josie—and later, Rob—pretend to be high students, despite having graduated years ago.
  • Betty and Veronica: Discussed. "I always preferred Betty, but Veronica had great legs."
  • Big Damn Kiss: At the end of the film.
  • Big Eater: Rob. He wins an eating contest by downing a five gallon bucket of coleslaw.
  • Big Man on Campus: Guy Perkins and later, Rob Geller.
    • In flashbacks, Billy is this at Josie's high school.
  • Brainless Beauty: 99.9% of the popular kids at South Glen High.
  • Chicago: Several Chicago landmarks appear, and a climactic scene takes place at Wrigley Field.
  • Cool Sword: The main reason Guy is excited to go to prom as Orlando from As You Like It is that he gets to carry a sword.
  • Coordinated Clothes:
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    • The group of mathematical enthusiasts go to a prom in matching outfits. It makes them feel secure.
    • The Girl Posse, now including Josie, all buy cardigans together.
  • Da Editor: Gus is hard on Josie and skeptical about whether she has what it takes to be a true journalist, but he clearly cares about her.
  • Dunce Cap: Actually a Dunce Sombrero. Josie has to wear it because she was late to class.
  • Embarrassing Nickname: Josie Grossie!
  • Embarrassment Plot: Josie’s major motivation is to redeem her high school experience after being traumatized by the most popular guy in school, who pretended he was taking her to the prom but then threw eggs at her when he came to pick her up. At the end, Josie becomes prom queen but sacrifices her own popularity to prevent Aldys from suffering a similar humiliation at prom.
  • Ethical Slut: Anita is a great friend and Foil to Josie. While Josie is a hopeless romantic waiting for that one Big Damn Kiss, Anita is way more sexually liberated but still hoping to find a true love.
  • First Kiss: Josie dreams of having her first great kiss, and finally gets it in the final scene of the movie.
  • Forced Meme: Guy proclaims "rufus" as the new cool word and tells his friends to spread it around. Because Guy is the Big Man on Campus, it actually works. And when one friend tries to spice it up by saying “rufulicious,” Guy insists that it’s just “rufus.”
  • Fundraiser Carnival: It is at one of these that Josie and Mr. Coolson share a ferris wheel ride filled with awkward UST.
  • Gilligan Cut: Rob enrolls in high school, so he can become a popular kid and then help Josie become popular. Josie scoffs at Rob’s arrogance in assuming he can become immediately popular, but in the next scene Rob has already won over the cool kids by winning an eating contest.
  • Girl Posse: Gibby, Kristen, and Kirsten are the three most popular girls at South Glen High, making one of these. Who the leader is isn't made clear, however. It seems to change from scene to scene.
  • The Grovel: Josie poses as a high school student and falls in love with her teacher, Sam. When it's revealed that she's actually a 25-year-old investigative reporter, she prints an apology in her paper and tells him to meet her at the baseball stadium if he accepts. Then she waits there with the whole town watching to see if she'll be accepted or rejected.
  • Gym Class Hell: Josie, being the more cerebral sort, really struggles during gym class. The Drill Sergeant Nasty teacher doesn't help.
    Gym Teacher: If you fail gym, you're never getting into college.
    Josie: You guys are still telling that lie?
  • High-School Dance: The climax of the movie takes place at the senior prom.
  • Hot for Teacher: Josie and Coulson fall for each other, so much so that Josie's bosses at the Sun-Times want that to be the focus of her ultimate story. Instead, Josie writes an open love letter to him, culminating in her First Big Damn Kiss.
  • Humiliation Conga: Poor Josie. She's late to class, forced to wear an embarrassing sombrero, fumbles her introduction by claiming that her family are sheep farmers, and spills chocolate milk down her white pants.
    • And again later. She's late again, coming down off a high, wearing the same clothes as the night before, has the word "loser" on her forehead, throws up on camera, and then is knocked out by a door.
  • Informed Attribute: Guy is the most popular guy at school and according to Josie, “the guy you get up to see at school,” but he does absolutely nothing that makes him stand out from any of the other students, except that they all look up to him.
  • Intoxication Ensues: Josie eats a brownie at a dance club. The man who gave it to her said it was rich in Vitamins T, H, & C!. She ends up passing out, and her hand-stamp ends up writing "loser" on her head.
  • In with the In Crowd: A large part of the plot.
  • Liar Revealed: Josie outs herself and her brother at the prom.
  • Of Course I'm Not a Virgin: For those wondering, yes, Josie's been kissed before. She's just never really been kissed.
  • Older Than They Look: Josie is chosen to go undercover as a high school student because she looks young for twenty-five, at least at the start of the movie. For some reason Josie actually looks a lot older when she's masquerading as a student, with her curled and unflattering haircut, heavy make-up and dowdy clothes. Josie in her work outfit is much more believable as a student.
  • Orbital Kiss: Josie and Sam in the end.
  • Popular Is Dumb: Oh so much. The only one that seems to have a rare moment of awareness is Big Man on Campus, Guy Perkins.
    • The Girl Posse can't even remember that Rosalind and Orlando are the main characters of As You Like It, the play they've been studying in English all semester.
  • Prank Date: Josie's real high school prom was a nightmare. As seen in a flashback, the most popular boy in school asked her to the prom but on the night of the prom, threw eggs at her from the limo with his actual date.
  • "Risky Business" Dance: For the Famous Couples Throughout History prom theme, Rob dresses up as Cruise in his dance scene from that movie.
  • Rom Com Job: Josie is a copy editor for the Chicago Sun-Times.
  • She Cleans Up Nicely: Done when Josie's prom dress is revealed. Interestingly, it's her brother, Rob, that reacts by telling her that she looks great.
  • Shout-Out:
  • Single Girl Seeks Most Popular Guy: Twice. Once when Josie really was a high school student (it didn't end well) and again when she goes undercover though she's more attracted to the age-appropriate Sam than to Guy.
  • Two-Teacher School: The kooky French/Spanish/Social Studies teacher and the English/Sex Ed teacher.
  • What the Hell, Hero?: Rob and Sam feel this way toward Josie after she reveals she is really a reporter pretending to be a high school student.
    • Sam is mad at Josie for lying about her true identity and almost setting him up for being attracted to her.
    • Rob is mad at Josie for outing him as well, ruining his chance to play high school baseball again.
  • Who Names Their Kid "Dude"?: A couple instances. When asked about her name, Aldys replies that her mother was 'going through her Harlequin romance phase' when she named her. Josie tries to reassure her that it's not any easier being named after a guitar playing pussycat.
    • Another example is Guy Perkins. When introduced to him, Josie doesn't realize that that's his name, not just his gender. It spirals out of control from there.
  • Worst News Judgment Ever: Roger Ebert, who worked in real life at the Chicago Sun-Times (where Josie is supposed to work), was amused by the film's portrayal of investigative journalism:
    "Josie's adventures in high school are monitored at the Sun-Times through a remarkable invention, a brooch that contains a miniature TV camera and transmits everything she sees back to the office. We do not actually have such technology at the Sun-Times, and thank heavens, or my editors would have had to suffer through "Baby Geniuses.'' [...] Apparently at both papers the way to get a big salary and an office is to devote thousands of dollars and weeks of time to an assignment where you hardly ever write anything."
  • Writers Cannot Do Math: If Josie is 25 in 1999, her senior prom would have taken place in 1992, not The '80s, as all of the flashback music and fashion would suggest.
    • But then again it was 1992, the part of the 90s where popular fashion and music from the 80s was still dying. Josie herself is certainly not aware of fashion trends.
    • Also that the value of "pi" during the bake sale is wrong. Might be forgivable for the average high school student, inexcusable considering this was supposed to be the "smart" class.

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