Grade retention is an educational practice that requires students to repeat the grade level they have just completed (Jimerson, 2001). In the United States, an estimated 15% to 19% of students are retained each year (Holmes, 2006). Previous research on grade retention is comprised of quantitative studies describing students who have been retained as having higher suspension rates, coming from a low socio-economic status, and having an increased chance of dropping out of school (Christle, Jolivette, & Nelson, 2007; Janosz, et al., 1997; Jimerson & Ferguson, 2007; Jimerson et al., 2002; Suh & Suh 2007). While these studies provide a wealth of information about grade retention, they do not describe how adolescents reacted when they were retained and how they experienced retention in their lives. In this qualitative study, eight students and one of their parents were interviewed about their experiences and reactions with retention. The dominant themes identified from student and parent interviews suggest that adolescent students and their parents believed that adolescent students reacted negatively to retention, experienced changes in their lives, experienced a loss of self-esteem, felt left behind by peers, felt older than peers, felt that retention added another year of school to their education, and that adolescent students’ school performance improved following retention. Implications for school counselors are provided.