Tomcats (2001)

At a friend’s wedding, a group of college buddies makes a wager: the last bachelor among them will win a shared cash pot. Seven years later, only Michael and one other man remain unmarried, and the kitty has grown to $500,000. After Michael loses $51,000 in Las Vegas, he needs the money fast, but collecting means getting the group’s other holdout, a hopeless womanizer, to finally tie the knot.