Tomcats (2001)

Synopsis
This romantic comedy in the vein of There's Something About Mary and American Pie concerns the story of Michael Delaney (Jerry O'Connell), a struggling cartoonist who makes a bet with seven buddies over who will be the last to marry. Several years later, the pot has boiled down to two: Michael, who is battling gambling debts in Las Vegas, and diehard bachelor Kyle Bremmer (Jake Busey), who is a self-proclaimed ladies' man. Michael tries to get Kyle to wed within 30 days in order to rescue himself from financial turmoil. When Natalie (Shannon Elizabeth) enters the picture as Kyle's new intended bride (as set up by Michael), she and Michael end up falling for one another, setting up a competition for her affections by the two men. Tomcats is the feature directorial debut for screenwriter Gregory Poirier. ~ Jason Clark, All Movie Guide