Ray Livingston, a self-proclaimed “freelance writer,” is behind the notorious Brooklyn blog, “Occasionally Dating Black Women.” Despite its controversial nature, the blog is well-crafted and has gained some fame. However, Ray feels trapped by his prolonged stay in New York, a lackluster love life, and a stalled writing career. After a particularly bad week, he lashes out at a beautiful stranger, only to realize she is Rochelle Marseille, a rising literary star in New York. Eager to repair his reputation, Ray is taken aback when Rochelle offers him more than he ever anticipated.