Vowing never to get married, six buddies contribute $1,000 each into a mutual fund with the agreement that the last single man gets it all. Seven years later, there are only two bachelors left - Michael (Jerry O'Connell) and Kyle (Jake Busey) and the kitty has grown to a half a million dollars. Desperate to pay off a huge gambling debt, Michael plots to get Kyle married by tracking down super-sexy Natalie (Shannon Elizabeth), "the lost love of Kyle's life". Through a little creative intervention involving a dominatrix librarian, a Las Vegas mobster, and a quick trip to a sperm bank, Michael and Natalie scheme to trick Kyle into unholy matrimony and split the money. But when Michael finds himself falling for Natalie, the dash for cash takes a wild turn in this raucous laugh-fest!