Sidney (Sanaa Lathan) and Dre (Taye Diggs) have been friends since they were ten years old. What brought them together? A love for a burgeoning new music style called hip-hop. 20 years later, Dre is the owner of a successful record company and Sidney is a respected and hard-nosed music journalist, and both are still friends... close friends. So close, in fact, that everyone around them is surprised that they haven’t gotten romantically involved with the other. When Dre proposes to his beautiful lawyer girlfriend Reese (Nicole Ari Parker), Sidney begins to question her own relationship with her boyfriend. As Dre’s wedding day draws near, Sidney begins to fear that Dre has always been the love of her life and she’s let him slip through her hands.