This chapter examines the different types of inter-racial relationships involving Black men by considering the responses of the men and to a lesser degree, by considering some of the ways that these relationships have been represented in popular culture. Black men in interracial relationships, who actively seek out such relationships because of their beliefs about the rewards they receive as a result of their affiliation with a woman who is not Black, form the type of relationship referred to an “obsession.” However, given the unique hostility directed at interracial relationships between Blacks and Whites, this aspect of rebellion may be most salient for Black/White interracial relationships. For the relationship characterized as an “obsession,” a preoccupation or fascination with specific attributes that are associated with the racial status of the partner exists. The Black man in an interracial relationship who is an “obsessor” pursues women who are not Black because of his beliefs about the meaning of observed differences.