Tomcats

At the wedding of a friend, the remaining bachelors bet on staying single. 7 years later, one of the 2 remaining loses $51000 in Vegas. He must get the other guy married to cash in and pay his debt or die. A cute woman helps him.
College buddies chip in and promise that the group's last unmarried man will collect a cash pot. Seven years later, the kitty is worth $500,000 -- money Michael needs to pay a gambling debt. Problem is, the only other single guy is a hopeless womanizer!