'''''Never Been Kissed''''' is a 1999 [[RomanticComedy comedy]] directed by Raja Gosnell and starring Creator/DrewBarrymore and David Arquette, It was produced by Drew Barrymore's [[ShamelessSelfPromoter production company]], '''Flower Films'''. [[Creator/DrewBarrymore Josie Geller]] is a 25-year-old journalist assigned to report undercover as a [[AdultsDressedAsChildren 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.
!!This film contains examples of the following tropes:
* AcquiredSituationalNarcissism: Averted at first, but then play straight for a while later in the film.
* BettyAndVeronica: Discussed. "I always preferred Betty, but Veronica had great legs."
* BigEater: Rob. He wins an eating contest by downing a five gallon bucket of coleslaw.
* BigManOnCampus: Guy Perkins and later, Rob Geller.
** In flashbacks, Billy is this at Josie's high school.
* BrainlessBeauty: 99.9% of the popular kids at South Glen High.
* BrotherSisterIncest: In order to make his sister more popular, [[BigManOnCampus Rob]] lied and said that he and her dated. Of course, they are both undercover and no one knows that they are siblings. Still kind of squicky, though.
* CoordinatedClothes: The group of mathematical enthusiasts go to a prom in matching outfits. It makes them feel secure.
* DawsonCasting: One of the reasons Drew Barrymore blended in; most of the other high school students were also in their mid twenties. Averted by Creator/JessicaAlba as one of the school's most popular girls ("Nuh-uh, I'm Disco Barbie!") and LeeleeSobieski - the movie was released just over a fortnight before Jessica's 18th birthday, and Leelee turned 16 a few months ''later''. David Arquette stands out in particular--he plays Josie's *younger* (age 23) brother, but is actually 3 years older than Drew Barrymore.
* DunceCap: Actually a Dunce Sombrero. Josie has to wear it because she was late to class.
* FundraiserCarnival: It is at one of these that Josie and Mr. Coolson share a ferris wheel ride filled with awkward [[UnresolvedSexualTension UST]].
* GirlPosse: 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.
* TheGrovel: 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.
* GymClassHell: Josie, being the more cerebral sort, really struggles during gym class. The DrillSergeantNasty teacher doesn't help.
-->'''Gym Teacher''': If you fail gym, you're never getting into college.
-->'''Josie''': You guys are still telling that lie?
* HighSchoolDance: The climax of the movie takes place at the senior prom.
* HotForTeacher: Played with.
* IntoxicationEnsues: 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.
* InWithTheInCrowd: A large part of the plot.
* OfCourseImNotAVirgin: For those wondering, yes, Josie's been kissed before. She's just never ''really'' been kissed.
* PopularIsDumb: Oh so much. The only one that seems to have a rare moment of awareness is BigManOnCampus, Guy Perkins.
** The GirlPosse can't even remember that Rosalind and Orlando are the main characters of Theatre/AsYouLikeIt, the play they've been studying in English all semester.
* PrankDate: 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.
* RiskyBusinessDance: For the Famous Couples Throughout History prom theme, Rob dresses up as Cruise in his dance scene from that movie.
* SheCleansUpNicely: Done when Josie's prom dress is revealed. Interestingly, it's her brother, Rob, that reacts by telling her that she looks great.
* SingleGirlSeeksMostPopularGuy: 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.
* TheWindyCity: Several Chicago landmarks appear, and a climactic scene takes place at Wrigley Field.
* TwoTeacherSchool: The kooky French/Spanish/Social Studies teacher and the English/Sex Ed teacher.
* WhoNamesTheirKidDude: A couple instances. When asked about her name, [[LeeleeSobieski 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 [[JosieAndThePussycats 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.
* WorstNewsJudgmentEver: Creator/RogerEbert, who worked in real life at the Chicago Sun-Times (where Josie is supposed to work), was [[http://www.rogerebert.com/reviews/never-been-kissed-1999 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 "Film/BabyGeniuses.'' [...] 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."
* WritersCannotDoMath: If Josie is 25 in 1999, her senior prom would have taken place in 1992, not TheEighties, 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.
** 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.