Factual error: In the scene where we first meet Rosie, it opens with a shot of the house and then goes inside, passing by some pictures of Rosie and her husband. One of them, a picture of their wedding, says "Frank and Rosie - Wedding 1948", but then when Rosie is talking about how her husband will know how much she still loves him after all those years, Robbie says that he hopes that he and Linda will be as happy as Rosie and her husband on their 50th anniversary. If they got married in 1948, they would be closer to their 40th wedding anniversary. Since the movie is supposed to take place in 1985, this would actually be their 37th wedding anniversary.
Continuity mistake: During the 50th wedding anniversary party, after Rosie is done singing, she walks over to her husband Frank and they embrace with her on the left, and him on the right. The camera cuts away to Adam Sandler, then back to them, only now Frank is on the left and Rosie is on the right. The camera cuts to Adam again, then back to the couple where they are in their original positions.
Continuity mistake: When Robbie (Adam Sandler) is lying in the trash dumpster, after he just got dumped, you can see him covered with trash. Then the camera switches to Julia (Drew Barrymore), and when it goes back to Robbie, there's different trash, and less trash, and it isn't in the same position.
Continuity mistake: At the cake shop for Glen and Julia's Wedding, Adam Sandler is feeding Boy George some samples of cake. First you see 2 pieces of cake on the plate. Then he feeds one to that weird person, and in the next frame with the plate it's empty. Then after that there is still one piece of cake on the plate.
Continuity mistake: When Robbie is singing at his first wedding back (Cindy and Scott's), just after George sings the backup "Holiday", Robbie then sings "It would be.." and when he sings this he lifts his left hand into shot and on his ring finger you can see something white in a ring shape around the top part of that finger, but in the next shot of him after it changes to a shot of the annoyed father and back, the white "ring" that was around his finger is no longer there.
Continuity mistake: In the scene where Robbie is back at his sisters house talking to his best friend and sister's husband, one of her children (dressed as Freddy) walks up with a picture of Robbie and Linda where he drew on Linda to make her look like the devil. When he hands the picture to Robbie, it is passed to him from the side, but in the next shot a split second later it is passed in front of him (facing frontwards) by the child.
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