Tomcats

Tomcats (2001), directed by Gregory Poirier, is a comedy starring Jerry O'Connell and Shannon Elizabeth.

The story concerns a group of friends who made a deal to put each invest in a fund, which would be paid to the last remaining bachelor of the group. Jerry O'Connell's character attempts to get the other remaining bachelor to get married, so he can claim the fund to pay off a gambling debt.