This study aimed to understand the role of adolescent and parent social media use on adolescents reported at-risk behaviors, as well as the role of social media among at-risk youths and their parents. Semi-structured interviews, based on interpretive phenomenological analysis, were utilized with six pairs of individuals resulting in 12 total participants. Each pair consisted of an adolescent between the ages of 13 and 17 along with their parent. Data analysis resulted in three themes: encountering negativity on social media did not refrain the adolescent from social media usage, misunderstanding of the parent regarding social media and technology caused challenges in parental monitoring, and the quality of time spent together differed in the perception of the adolescent participants and parent participants. The findings of this study suggest that even though participant pairs reported encountering negativity on social media, they continue to use social media, and parent participants are unaware of the amount of time their adolescent spends on social media, which could be contributed to the lack of quality time they spend with one another. The findings of this research add to the current literature regarding social media and the impact it has on the parent-adolescent relationship among at-risk youth.