The only black guy in his indie-rock social scene, Jay Brooks(30 going on 21) is witty and opinionated. A story board artist by trade, and sci-fi junkie, he is quite the sexual overachiever in his indie rock world. Still, Jay feels unfulfilled as he watches Drake, a high school buddy, preparing for marriage. Drake Moore, a tall and handsome black lawyer, has Alpha Male credentials, but is nevertheless controlled by his fiancée, J.C. who comes from a high strung, well-to-do family. Drake wants to give J.C. the wedding of her dreams, but he sweats over juggling their families’ economic and class prejudices of one another. As Jay takes stock of his many failed relationships, he notices a common denominator: all the women were white. Matt, Jay’s best friend and roommate, calls him on blaming his issues on white women, but Jay insists he is right. Jay gives up dating white women “cold turkey,” and goes in search of the perfect “sistah.” Unfortunately, he doesn’t fit the current stereotype of the hip-hop loving, b-boy baller from rap videos. Jay crashes and burns with the “sistahs” and, quite by accident, his quest leads him to Catherine, an un-Orthodox black woman. Meanwhile, Matt struggles to attract the attentions of Molly, a woman who works in a hip-hop record store. A bit of a nervous fellow, and equally opinionated, Matt and Jay are friends from art school and their relationship centers on their love of comic books, cartoons, movies and music. Catherine is an up and coming fiction writer. A lover of tobacco and alcohol, Catherine was raised in the Valley, has a therapist in Hollywood, and considers the beach her second home. Although a neurotic Valley girl at heart, Catherine is an old soul. She initially resists Jay’s advances but is unconsciously drawn to his unique personality. At his behest, Catherine faces her fears of reading her newly published work in public. Matt applies to work at the hip-hop record store in order to better court his crush and, after a severe cram session, he barely passes a pre-requisite hip-hop exam. Matt is pained to then discover that Molly has a boyfriend. Jay’s budding relationship with Catherine, and Matt’s thwarted effort with Molly, stretches their friendship in unexpected ways. The two are forced to see one another in a new light, and the growth their friendship experiences is the catalyst for the maturation of their relationships with women. As Jay’s feelings deepen for Catherine, he must address his commitment issues, the real root of his problems, in order to win her
