Factual error: In the very first scene in the film when the magazine covers are flashing up, the very first one has a headline which says "loose that belly". For a film whose title has the word "lose" in it, you'd think that they could spell this properly.
Factual error: When the 3 guys are trying to think of a slogan for the new diamond gig, Matthew McConaughey (Ben) suggests that they go play a game of 9 Ball to clear their minds. However, he racks up every ball in the triangle, which means they would now be playing 8 Ball.
Factual error: In the scenes where Andie and Ben are at the NBA Finals games, it always shows a shot of the basketball players. When the clock is winding down, and it is supposedly a very close game, it shows the bench players of the Sacramento Kings on the court. Players such as Lawrence Funderburke, Gerald Wallace, and Scot Pollard only play when there is a huge difference in the scores of the teams, but in the movie, they are supposedly playing a very close ball game. Also, this movie takes place in 2003, which is the year that the Kings got new uniforms, so they wouldn't be playing in the ones that they were wearing. Also, when a team in the NBA enters a finals game, they wear new jerseys that have the NBA Championship Trophy stitched onto them. In the movie, neither team had this on their jerseys.
Factual error: In the scene where Ben is bringing Andie back to his apartment after meeting her for the first time, you see the two helmets on tables in the living room, when obviously they just wore them on the motorcycle ride to the apartment. (00:23:45)
Factual error: The Knicks are supposedly playing at home for games 1, 3, and 7 of the NBA Finals during the course of the film. This is not possible for two reasons. First, games 1 and 3 are never played in the same location(either 2-3-2 or 2-2-1-1-1). Second, if the NBA Finals were to extend to 7 games, this would typically take place over two weeks and not the 10 day premise of the film.