Continuity mistake: In the opening shots we see Chris writing in Jamie's yearbook. However between shots it is evident that the handwriting has changed position and style. (00:00:35)
Other mistake: When Chris and Jamie are sitting on Jamie's bed, Tim comes in and shoves Chris onto the floor. This is supposed to be when the yearbooks are switched, but if you watch closely you will notice that Tim leaves with the same yearbook he brought in. (00:03:50)
Continuity mistake: After Chris puts the 'Shakes come and go but friends are furrr-ever' tee-shirt on, the position of the black collar sticking out from the tee underneath keeps changing. (00:05:50)
Continuity mistake: Chris walks out of the elevator with another worker, who is holding a pile of presents. Betweens shots an extra present appears on the pile, so Chris can pick it up and give it to Francine. (00:11:20)
Continuity mistake: The position of Samantha's guitar strap changes as she is singing her song in the recording booth. It jumps off of her shoulder between shots as well. (00:14:50)
Continuity mistake: When Chris is at the recording studio with Samantha, when Samantha runs and jumps onto Chris, the position of her belt changes a few times from tight to loose. (00:15:50)
Continuity mistake: After Samantha jumps on Chris and undoes his trousers, she runs to the other couch and plays her song. As she sings it the magazines on the table in between them change between each shot. (00:16:15)
Continuity mistake: When Tim is talking to Chris in The Maple Tavern, he is drinking a beer. The foam on top of the beer keeps disappearing and reappearing between shots. (00:26:00)
Audio problem: In the bar after Chris sees Jamie, she says, "Wow! Your arms, and your belly, and pecks! Chris Brander." After Chris laughs while she's telling him that his mouth is moving but he isn't saying anything. (00:26:00)
Continuity mistake: When Chris and Jamie are on their day-date in the diner, Chris is holding a fork as he talks to Jamie. The direction of which the tines on the fork point changes between shots. (00:30:35)
Revealing mistake: When Chris and Jamie are on their day date in the diner, Jamie has a grilled cheese sandwich with ranch on the side. However it is obvious that the bowl of ranch is empty. (00:33:10)
Continuity mistake: The water glass on the table disappears and reappears a few times. (00:34:00)
Continuity mistake: When Samantha is sitting at the foot of the bed with an ice pack on her head, eating toothpaste, in one shot she spits some toothpaste out and it goes over Chris' hand. In the next shot his hand is clean. (00:36:55)
Continuity mistake: During the ice hockey scene, while Chris is barreling through the kids, the puck is nowhere to be seen despite the puck handling motions. (00:44:40)
Revealing mistake: After the group of four see "The Notebook", when Jamie, Chris and his mom are watching the home videos of Chris and Jamie, the latex makeup is starting to peel off Chris's face.
Plot hole: In the yearbook scene Tim barges into Jamie's room and asks her to sign his yearbook, pushes Chris off the bed, and they somehow get their yearbooks mixed up. Tim's yearbook is left in the room with Jamie and Chris, while Tim takes Jamie's yearbook that Chris wrote in with him. When Chris asks Jamie to read the message he wrote in her yearbook, she instead reads the message that Tim wrote to her in his own yearbook. If Tim was asking Jamie to sign his yearbook, why would sign the yearbook with as if he was signing Jamie's. If he was intending to sign Jamie's yearbook, he would have written in the same yearbook that Chris wrote in and not his own.
Continuity mistake: In the scene when Chris and Jamie are watching old home videos Chris has on braces, but when he brings her home he doesn't have them.
Deliberate mistake: In the beginning Chris and Jaime are on the bed talking and she is excited about graduating she is wearing a mini dress. In the shot where she falls face down in his lap and her dress goes up, she's wearing black tights underneath her dress, which are not there in any other shot.
Revealing mistake: After the first "day date", Chris gets into the Porsche and spazzes out while Jamie watches. She can't hear him because the windows are up, but as the camera moves into frame and into the car you can tell that the passenger-side window is down, presumably to allow for sound and camera entry.