I'm Through with White Girls (The Inevitable Undoing of Jay Brooks) 2007

Name: I'm Through with White Girls (The Inevitable Undoing of Jay Brooks)
Released: 2007-02-01
Cast: Anthony Montgomery, Ryan Alosio, Lia Johnson, Lamman Rucker, Kellee Stewart

Synopsis:

Jay Brooks is that black guy who digs indie rock, graphic novels, and dates white chicks. After a slew of bad break-ups, Jay gives up white women, "cold turkey," and he goes on a mission: "Operation Brown Sugar". But because Jay doesn't fit the "brotha" stereotype, he fails miserably with the "sistahs." Then he meets the dynamic Catherine, a misunderstood "Half-rican Canadian", who's as righteously quirky as he is. To win her heart, Jay must confront his fears as he realizes commitment is a bigger issue than race.