Tomcats (2001)

In "Tomcats" (2001), a group of friends make a bet to see who can remain single the longest in order to win a large sum of money. Michael, one of the friends, attempts to win by getting a woman to marry him and then get a quick divorce. However, he falls for the woman, creating a dilemma for him and his friends. As their antics escalate, the group's relationships and loyalties are tested in unexpected ways.