Emotional Backgammon  (2000)

Theatrical Release Information:
Emotional Backgammon

Actor Leon Herbert made his debut as a writer and director with this independent comedy drama. John (Wil Johnson) is a tailor who likes his work and is happy with his girlfriend Mary (Daniela Lavender) -- enough so that he asks her to marry him; however, Mary not only declines the offer but decides it's time to split up and spend some time working on her own emotional issues. Eager to win her back, John turns to his best friend Steve (Leon Herbert) for advice. Steve, an actor who has been rehearsing a role in Shakespeare's The Taming of the Shrew, takes an aggressive view of the situation and recommends a strategy not unlike his take-no-prisoners approach to backgammon. Meanwhile, Mary also confers with a friend, Jane (Jacqueline de Peza), whose attitude towards men is not especially charitable. ~ Mark Deming, All Movie Guide