Never Been Kissed

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

Josie Geller 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.

Tropes used in Never Been Kissed include:

Acquired Situational Narcissism: Averted at first, but then play straight for a while later in the film.
Adults Dressed as Children
Big Man on Campus: Guy Perkins and later, Rob Geller.
Brother-Sister Incest: In order to get his sister more popular, 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.
Chick Flick
Dawson Casting: One of the reasons Drew Barrymore blended in; most of the other high school students were also in their mid twenties. Averted by Jessica Alba as one of the school's most popular girls ("Nuh-uh, I'm Disco Barbie!") and Leelee Sobieski - the movie was released just over a fortnight before Jessica's 18th birthday, and Leelee turned 16 a few months later.
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.
Hot for Teacher: Played with.
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
Of Course I'm Not a Virgin: For those wondering, no, Josie's been kissed before. She's just never really been kissed.
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 - and on the night of the prom, threw eggs at her from the limo with actual date.
Risky Business Dance: In a Famous Couples prom theme, Rob dresses up as Cruise in his dance scene from that movie.
Romantic Comedy
Two-Teacher School: The kooky French/Spanish/Social Studies teacher and the English/Sex Ed teacher.
Writers Cannot Do Math: If Josie is 25 in 1999, her senior prom would have taken place in 1992, not The Eighties, as all of the flashback music and fashion would suggest.
- 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...