History Film / NeverBeenKissed

** But then again it was 1992, the part of the 90s where popular fashion and music from the 80s was still dying.

* HumiliationConga: 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. That's just the first day, things get much worse for her.

* 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.

* 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 Creator/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.

* 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.

* 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]].

* TheWindyCity: Several Chicago landmarks appear, and a climactic scene takes place at Wrigley Field.

'''''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.

* 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''.

--> "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 "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."

** 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...

** Possibly, but YMMV, since the first few years of the new decade often resembles the last few of the old one. 1992 could easily have had enough in common with the late '80s (or the stereotypical perception thereof) to have this effect. Or, it could have just been an 80s-themed prom?
** The above is debatable. What is not up for debate is 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...

'''''Never Been Kissed''''' is a 1999 [[RomanticComedy comedy]] directed by Raja Gosnell and starring DrewBarrymore and David Arquette, It was produced by Drew Barrymore's [[ShamelessSelfPromoter production company]], '''Flower Films'''.
[[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.

* Big Eater: Rob. He wins an eating contest by downing a five gallon bucket of coleslaw.
* BigManOnCampus: Guy Perkins and later, Rob Geller.

* BrotherSisterIncest: In order to get 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.

* 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.

* InWithTheInCrowd: A large part of the plot
* OfCourseImNotAVirgin: For those wondering, no, Josie's been kissed before. She's just never ''really'' been kissed.

* 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 - and on the night of the prom, threw eggs at her from the limo with actual date.
* RiskyBusinessDance: In a Famous Couples prom theme, Rob dresses up as Cruise in his dance scene from that movie.

* SheCleansUpNicely: Throughout the movie, Josie's clothing and personal style becomes more fashionable. This isn't generally remarked upon except to point out how ''badly'' she was dressed before.
** This trope really comes into effect when her prom dress is revealed. Interestingly, it's her brother, Rob, that reacts by telling her that she looks great.

** The GirlPosse 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.

* 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.

* SheCleansUpNicely: Through the movie, Josie's clothing and personal style becomes more fashionable. This isn't generally remarked upon except to point out how 'badly' she was dressed before.

* 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.

* DawsonCasting: One of the reasons Drew Barrymore blended in; most of the other high school students were also in their mid twenties. Averted by 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''.

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