The study explored the experiences of 35 children of former Arkansas Single Parent Scholarship Fund awardees through qualitative interviews. Particularly, the study sought to understand their experiences in single-parent households, before, during, and after their parents pursued a college degree as well as how they perceived the impact of the scholarships, especially in relation to their own educational attainment. From the qualitative interviews, three main areas were identified: the hardships of single-parent households, the challenges and possibilities of single parents’ higher education, and the generational impact of the Arkansas Single Parent Scholarship Fund. For each area, themes and subthemes were identified along with their thick description. The findings of the study emphasize the significance of single parents’ educational and economic accomplishment in children’s education and quality of life even though they also note the challenges within single-parent households, especially during the parents’ college years. The implications of the findings are discussed.