Kenya McQueen (Sanaa Lathan) is a successful, single African-American woman, whose time is consumed by her competitive job as a CPA. As soon as her life becomes all work and no play, her successful job and her new home are over shadowed by loneliness and her obsessive compulsive desires for perfection. Urged on by her friends to try something new, she tries letting go of her dream of the ideal black man. Subsequently, Kenya accepts a blind date set up by her co-worker Leah, who is in the process of planning a wedding that Kenya often dreams about. Her date, Brian Kelly (Simon Baker), a handsome and free-spirited caucasian landscape architect, is rudely turned down when Kenya sees that he is not at all what she expected.
Soon, the two meet again at a party, and though he isn t what she pictures for herself, Kenya hires Brian to landscape her desperate backyard. Over time, Brian begins to make Kenya see a different side of herself and she starts to like the way it feels to be spontaneous, but Kenya can t help to shake off her reservations about their romance. The opinions of her girlfriends, her affluent parents, and her womanizing younger brother begin to have a negative effect on how she views her socially tested relationship with Brian and inevitably, their differences pull them apart. But, when Kenya s perfect black man, Mark (Blair Underwood), enters her life, everything she thought she wanted is challenged and nothing seems to make her feel as alive as she felt with Brian. When the dissonance that she s created in her mind finally overwhelms her, Kenya chooses to go after Brian, no longer allowing her own controlling nature and social norms to dictate the matters of her heart.