Unlucky in love. Unlucky period.

Best friends Les (Grant Shaud), Al (Will Ferrell), and Nick (Anthony Palermo), who were born 33 years ago on the same day in the same hospital, spend their collective 33rd birthday getting rejected by a variety of women in a nightclub.

In desparation, Les proposes a bet to try and lift them out of their romantic doldrums. He suggests that they each put two thousand dollars in a bank account, with the winner being the onre who can not only get a girlfriend, but also live with her for three months. Once Nick and Al reluctantly agree to the bet, bad things happen. Very bad things.

Using personal ads to begin their girlfriend quest ends in disaster. Nick then decides to hoodwink his two friends by faking a relationship with Celia, an old girlfriend from college (Pamela Gien), while Al proceeds to embark on a series of the worst first dates of all time. Les finds himself getting deeplyy involved with an alluring but mysterious woman (Starr Andreeff), who may or may not be married to a mobster.

The attempts by all three to win the bet lead to unexpected consequences and a surprising outcome.

Grant Shaud
Will Ferrell
Anthony Palermo
Starr Andreeff
Pamela Gien

Written, Produced
& Directed by:
Jim Milio

An MPH Entertainment Production