In the scene where Lindsey accepts the promotion, there is a group of people from the office. The guy in the front of the group with the goofy smile is Dr. Charles Steinburg, a member of the Red Sox front office. See more...
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Factual error: Towards the end of the movie, when they go to game four of the ALCS the announcer at the stadium announces: "Now batting John Olerud" but John Olerud didn't play in game four of the ALCS because he hit his foot with his bat during game 3 of the ALCS.
Factual error: In the opening day clips, they show 49, Tim Wakefield, starting. The starting pitcher that day was 38 Curt Schilling (Wakefield never played that day). Furthermore, the clips show them playing against the Texas Rangers; opening day 2004 was against the Toronto Blue Jays.
Continuity: When they show a highlight from ESPN when Drew Barrymore gets hit with a foul ball, Miguel Tejada is supposed to be at bat. The clip shows some random guy taking a cut and fouling the ball off. Not a big deal I guess, but I noticed it quickly.
Continuity: When Drew Barrymore is talking to her mom after her dad has just walked out of the kitchen, you see the teapot facing towards the right of the screen. However, in the next shot of it, it is facing the other way, towards the left.
Continuity: Ben is lounging around and watching a Sox game on TV. The first shot showed a lot of stains on his shirt. Between shots the stains vary, with at least one shot with hardly any stains at all.
Continuity: When Lindsey takes off her shoes and starts running to Ben, the shoes she took off are gone from the field in the following shots.
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.
Continuity: When one of Lindsey's friends gets hit during boxing practice at the gym, the size of the sweat marks on her shirt changes between shots.
Other: Near the end when Lindsey goes to Fenway to stop Ben from selling his tickets, she borrows binoculars from someone to find him across the field. She's looking through the wrong end. The way she's holding them, everything would look tiny, and yet she still sees him.
Continuity: Drew Barrymore gets hit with the baseball right below her left eye; yet, when she is on Jimmy Fallon's bed, it is her forehead that is swollen.
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.
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