The release date for the film was pushed back after the similarly-themed Chasing Liberty (2004) flopped at the box office. This movie flopped even harder.
When Samantha (Katie Holmes) and Mia (Amerie) are sliding down the slope on the Slip 'N Slide, Holmes inadvertently pulled down Amerie's sweatpants while struggling to climb over the hay bales, exposing Amerie's bottom in view of the camera. Director Forest Whitaker chose to leave this in the final cut of the film, since it was a spontaneous event, and quite in line with the carefree nature of the scene.
Vera Wang designed all of Katie Holmes' ballgowns for this film. (Her originals usually retail for over $10,000 each.)
The movie James (Marc Blucas) and Samantha (Katie Holmes) are watching in the movie theater is The Girl Can't Help It (1956). Director Forest Whitaker originally was set to direct a remake of the 1956 comedy after the release of this movie.
There is a scene where Samantha (Katie Holmes) climbs down a ladder in bare feet. In the DVD commentary, Holmes remarked that she was able to do only a single take because the rungs hurt her feet so badly.