Tomcats

"Tomcats" is a 2001 American sex comedy film about a group of college buddies who chip in and promise that the last unmarried man among them will inherit a cash pot, which Michael Delaney (Jerry O'Connell) mistakenly thinks belongs to him. He teams up with Officer Natalie Parker (Shannon Elizabeth), a woman he meets while trying to prevent a bachelor party from going ahead. As they try to outsmart their friend Kyle (Jake Busey), a womanizer who's now the only eligible bachelor, Michael finds himself falling for Natalie, who's working undercover.