March 30, 2001
Genre(s): Romantic Comedy
Seven years after a group of friends invest in a fund that will go to the last remaining bachelor, only Michael and Kyle are still in the running. Michael desperately needs Kyle to get married so he can get the money to pay off a gambling debt. The problem is that the only woman Kyle is interested in is not only not interested in him, but also the woman with whom Michael is secretly in love. Michael finds himself in all kinds of complicated situations as he tries to get Kyle married off, sell enough possessions pay his debt and keep the angry mobster at bay, finally shed his commitment phobia and tomcat reputation and find a way to profess his true love.