Towards the end, Lindsey and Ben are shown kissing on the field right after the Red Sox win the World Series. That shot was actually filmed moments after the Sox won the World Series on the field on October 27, 2004. See more...
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Factual error: In the scene in the park where Ben does his fake proposal bit and asks Lindsey if she'll go to opening day with him, the ticket is for Tuesday April 11th. It's obviously fake for two reasons. First, the Red Sox opening day in 2004 was April 9th, not the 11th. Second, April 11th, 2004, was a Sunday, not a Tuesday.
Continuity: When Lindsey is at her parent's house during spring break, they are discussing her father's hair. In the shot when her mother opens the fridge there are only 5 cookies on the plate, but when the shot changes and Lindsey is grabbing some cookies there is a whole plate of them. And the honey pot is missing too.
Factual error: When Ben and Lindsey have their fight over going to Paris, Ben says he can't because the Mariners are coming to town (his schedule on the chalkboard says 9th-12th). The Sox did play the Mariners on the 9th-12th, but it was in Seattle, not Boston. Also, when Lindsey says "Pedro's pitching Friday", Ben answers, "Saturday, Schilling's on Friday". Schilling did pitch that Friday, but Bronson Arroyo was the Boston starter on Saturday. Pedro Martinez didn't pitch again until the 14th, against the Devil Rays.