Continuity mistake: When Ronald is in the store talking to Cindy about renting her and the salesman is looking at them through the telescope, Ronald has the money in his hand fanned out. When the camera cuts to the store, the money is not fanned out in his hand anymore.
Continuity mistake: When Ronald has his first lunch with Cindy, the Coke can on this tray hops all over the place between shots.
Continuity mistake: In the gym dance scene, the actor who plays the African-American nerd who replaces Ronald is seen at one point dancing behind Ronald (presumably as an extra) while he should be in the gym's bleachers with Ronald's former nerd friends.
Continuity mistake: When Cindy has given Ronald a ride home from school, they arrive at her house and as she exits her car, her purse is on her shoulder. In the next shot, her purse is hanging on her arm and she lifts it up to her shoulder.
Continuity mistake: In the beginning when red wine is thrown on to Cindy's suede outfit, the pattern and intensity of the stain changes from when it's first thrown on her, to the bathroom, and then again when she's showing the man in the clothing store.
Continuity mistake: When Ronald is talking to Kenneth in Science class the first morning he and Cindy are acting as a couple, Ronald's position changes. In one scene his back is completely to the table and the next he's leaning on his right side facing Kenneth.
Continuity mistake: During the opening credits, Cindy and friends are shown driving up her driveway in a white VW Cabriolet sporting a red Arizona license plate on the front bumper. Scene cuts to Patrick Dempsey, then back to the VW, now parking - the license plate has disappeared.
Continuity mistake: In the scene where Ronald is fixing his tie, telling his parents and brother about his date with Cindy(while the mom and brother are playing Battleship), the Papasan Chair behind Ronald changes position from the beginning of the scene to the end of the scene. In the beginning and end the chair is in an upright position, during the scene with Ronald, the chair is in a flatter position.
Continuity mistake: When the song "Dancing With Myself" was playing, Patty took down the clock and said that it was 11:27pm. But after Cindy threw her drink on the record to stop it and made her speech, and Big John told Ronnie to get out of his house, the clock said it was 11:57pm. That means that the song would have had to be about 30 minutes long.
Continuity mistake: In the scene at the New Year's party, when Ronald and Iris come out of the bathroom and into the living room, Big John offers them both a beer, and it is a yellow can (Miller). Right after that when Bobby shows up, they are now all holding Budweiser cans.