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...) (00:25:20)
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. (00:50:00)
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. (00:04:50)
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. (00:36:25)
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. (00:12:50)
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. (00:14:55)
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. (00:30:35)
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. (00:30:20)
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. (00:20:20 - 00:22:00)
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. (00:58:15)
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. (00:13:20)
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. (00:08:20 - 00:09:10)
Continuity mistake: When Josie meets the female teacher, the teacher complains about not taking her medication, waving her arms expressively. In the next shot of her and Josie, the teacher's arms are clasped in front of her. (00:16:15)
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. (00:04:50)
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. (00:21:30)
Continuity mistake: In the sex talk class, you can see when Anita grabs the banana off the desk there's only about four bananas on the desk. In the next scene you can see there are about a dozen bananas all piled up.
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: 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. (00:11:20)
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. (00:13:20)
Revealing mistake: After Josie eats the chocolate cake, she starts dancing wildly on stage and does the splits. You can tell it's a stunt double that does the splits because the blond hair is nowhere near as curly.
Answer: Over the course of the evening, Guy learns that being popular isn't the most important thing in the world and wanted to make peace with Aldys. I think he was genuinely being a nice guy and wasn't in on the prank.