The purpose of the study was to investigate how grade retention affects Black males' perspectives about education and social-emotional skills during and after their K-12 educational journey. As a result of the Black Lives Matter movement, there has been increased discourse about our nation's current reality regarding the status of Black males--specifically, their experience in the educational environment (Wood, 2019). Black males are often "devalued and over-criminalized" (Wood, 2019, p. 1) resulting in an "overrepresentation in special education classes, higher rates of suspension and expulsion, and ultimately feeding the school-to-prison pipeline" (Wood, 2019, p. 1). Minimal attention has been dedicated to the emotional functioning of Black males and the internalizing factors that are strong predictors of their well-being later in life (Brown et al., 2013). Critical Race Theory (CRT) and the Big Five Social-Emotional Model were referenced in this study as relevant theoretical frameworks. The researcher conducted a qualitative phenomenological study investigating five African American males who experienced grade retention while attending a public school during their K-12 educational journey. The participants' ages ranged between 27-57 years. Seven themes were generated from their stories. The themes were (a) motivation (b) culturally responsive teaching (c) empathy (d) accountability (e) relationships/social engagement (f) embarrassment and (g) emotional trauma. The findings of this study further inform the fields of education, psychology, and sociology associated with the two research questions: How does the experience of grade retention affect perspectives about education among Black males? How are social-emotional skills affected among Black males who have experienced grade-level retention during their K-12 educational journey? Study findings have specific implications for practice, policy, and research. These include suggestions for alternatives to grade retention, culturally relevant teaching practices, and social-emotional learning instructional practices. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]