Adams was originally Smith's choice for the role of Bethany, but in order to get the movie made, he had to make some consessions, and one of them was that Adams wouldn't play the lead role. Adams was later set to play Serendipity, but Harvey Weinstein told her it probably wasn't a good idea for her to be in the film since she and Kevin Smith has just broken up.

Kevin Smith decided against casting Adams as Gertude for fear her pairing with Ben Afflek was too similar to Chasing Amy.