The trend of higher enrollment patterns among Black females when compared to their Black male counterparts is pronounced. For example, females comprise 65% of the Black student population on college and university campuses across the country (NCES, 2005). The grave imbalance between Black women and Black men in college raises several issues that have been ignored regarding the social adjustment and psychological well-being of Black women college students. The purpose of this article is to add to the discourse regarding current dating dilemmas confronting Black female college students. Racial identity development theory, the womanist identity development model, and Black feminist thought serve as a framework for understanding the challenges and outcomes of Black female college students relative to dating decisions and opportunities. Additionally, commentary regarding hip-hop among millennial college students is presented to highlight the significant impact that this culture has on the dating dilemmas and identity development of Black college women.