Factual error: In the montage sequence showing Drew Barrymore hanging out with the math club, they have a Pi poster with 3.1457869986. Only the first 3 digits are actually correct. (Pi = 3.1415926535897...)
Revealing mistake: When Rob is in the Cafeteria eating all the coleslaw, he yells "I'm the coleslaw king of the world!" there is a girl in the background who mouths it as he is saying it.
Continuity mistake: In the part when Josie doing sprints in gym class, she stops and holds on to the gym teacher's shoulders, with both hands, and begs for water. When the camera switches to behind the gym teachers head, Josie's hands aren't on the gym teacher's shoulders. When the camera goes back to behind Josie's back, her hands are back on the gym teacher's shoulders again. This happens several more times throughout the movie.
Continuity mistake: Pay attention to the lunchroom scene at the beginning of the movie. As Molly Shannon sits down, she is seen opening a bottle of water. The next time you see her the bottle is in the shot but the lid has never been taken off. The next time you see her, the bottle is nowhere to be found.
Continuity mistake: After George has put the wings on Josie's lapel, he waves his hand in front of the pin to make sure it works. As Josie gets out of the van, you can see on the screen that her pin is working. However, after she leaves the van, George has to turn on the TV screen and adjust some knobs before he picks up the video.
Other mistake: When Josie just arrives to the school and is standing with her back to the car, we see a blonde girl with a short blue dress pass, in the next shot, she passes again.
Continuity mistake: In the scene where Josie is in the toilet in the tiki post you see her break the chain, however when the camera shows her just before her flashback you can see the chain handle behind her again.
Continuity mistake: In the scene where Aldys and Josie drive by The Court, Guy comes up and makes fun of Aldys. Watch each shot angle in that scene. First Guy comes up and looks in through the window. Then when the camera changes angles, he has his arms resting on the window frame, and it goes back and forth through out that part.
Continuity mistake: In the scene where Aldys and Josie drive by the Court, Aldys' sister is in the back seat of the car. When they drive off, her sister is missing, next shot she is back.
Continuity mistake: In the scene where Josie is talking to the 'Popular' girls in the canteen on her first day you see a couple walk past behind her on the left (a man in a blue shirt and a girl in a sixties style dress). When Guy turns up, the couple walk past again in the same direction. This happens again with the same couple outside at the end of shool when Josie and Aldys are talking about their names. You see this couple a bunch of times during the movie.
Factual error: Also shortly after the boy is shown he walks towards Drew and goes to dump his soda in her bag. The Pepsi One can turns into a Sprite can of new design, rather than the design which would have been used at the time.
Continuity mistake: In the scene where the first board meeting is taking place, Anita has on dark lipstick, which you can see while she is licking the pencil. Afterward, when Josie runs out, Anita follows and when they reach Josie's office, you can see that Anita has no dark lipstick on at all.
Continuity mistake: During the sex talk with the kids are putting the condoms on the bananas, watch the curves of Josie and the blonde headed girl's bananas. They switch throughout the different scenes.
Other mistake: In the scene where the Denominators are versing the other school in a calculus competition you see everyone sitting at the table but when Josie wins she looks up and all of the team are around her chair. They couldn't have gotten up that fast.
Continuity mistake: In the beginning during the lunch scene Molly Shannon puts her fork down to open her water bottle but in the next scene the fork is in the Chinese food box.
Continuity mistake: In the scene where Josie walks out of the house and sees Guy pulling up in the limo, the part in her hair changes from one shot to the next.
Continuity mistake: In the lunchroom scene where Josie is telling her coworkers what a "real" kiss should feel like, the amount of sunlight coming in through the window changes between shots. In one shot, Josie's hair and face are matte, but in other shots her hair and the left side of her face is illuminated by sunlight. All the shots in this scene appear to have been filmed at different times of the day.
Continuity mistake: In the movie there is a scene where Drew Barrymore is remembering high school. It shows a boy walking towards her holding a Pepsi One can. Pepsi One was invented in the late nineties and would not have been around during the time this scene was supposed to have taken place.
Continuity mistake: In the scene where Josie and Aldys pull up to the court, the sidewalk beside the car is completely deserted. In the far distance, you can see people hanging out and congregating around garbage cans. Then in the very next shot, Guy is suddenly knocking on Josie's window. There's no way he would've had time to make it all the way from the congregation of people to the car that quickly.
Continuity mistake: In the pie-throwing scene, the camera shows the blond football player getting hit in the face with the first pie at the beginning of the contest. In the next shot, there are several pies sticking to the wall as if the contest had been going on for a while.
Continuity mistake: This mistake happens when Josie is at the 'Tiki Post' with Rob. When she is talking about how she gets to go back to high school, the strap of her handbag is across her chest, then the camera shoots to Rob and you can see Josie still in the camera's view and she doesn't move. But when they shoot back to Josie the strap of her back has moved.
Continuity mistake: In the VHS, when Josie is in the bathroom at the Tiki Post, and before she has the flashback in which toilet paper is put in her bookbag, she pulls the sheets of toilet paper off the roll. You can see in the lower left corner that the toilet paper is hanging off the roll - making it easier for her to pull it off and have it flow like it does.
Continuity mistake: In the scene when George first begins to flip on the monitors in the van on the first day of his surveillance of Josie, he is not wearing headphones. In the shot that immediately follows, it changes to another angle of George and headphones suddenly appear on his head.
Continuity mistake: At the end of the film after Sam kisses Josie, it cuts back to the audience and couples kissing each other. When one of the popular girls is kissing her boyfriend, you see right behind them the other popular girl hitting the guy that tried to kiss her and then she turns around. The very next scene is when he tries to kiss her and she starts hitting him again.
Continuity mistake: When Josie and the teacher kiss the first time, Jose has her hands on the teacher's shoulder's, the next shot of the same scene, her hands aren't on his shoulders.
Continuity mistake: Josie and Sam are painting the backdrop for the prom. Josie puts paint on Sam's face and he tries to get her back, but when Josie's work people watch the footage you see her putting the paint on Sam's face and then he wipes it off before trying to get her back.