Introduction <p>The innate desire to belong and form emotionally supportive bonds is a fundamental human need and a cornerstone of human existence. When the need for belonging is left unfulfilled, feelings of isolation can prevail. </p> Objective <p>Using data from the 2021 Monitoring the Future study, a nationally representative dataset, this article investigated factors associated with two forms of youth disengagement—social disconnectedness and educational disengagement—among U.S. adolescents in 8th and 10th grades (<i>N</i> = 23,238), focusing on the empirical link with remote learning, media usage, and familial, educational, and peer influences. </p> Method <p>Data were analyzed using multiple regression analyses, with the Full Information Maximum Likelihood as the estimation procedure. </p> Results <p>Overall, this study found a significant association between social disconnectedness and educational disengagement. Specifically, when youths disengaged from school, they also became socially disconnected. Further, remote learning was linked to increased social disconnectedness, but not educational disengagement, while media usage was connected to both forms of disengagement. The relationship between educational disengagement and social disconnectedness was more pronounced in males than females, while high media usage appeared to buffer the effects of social disconnectedness on educational disengagement. Additionally, parental involvement, education-related factors, and youths’ social engagement were significantly associated with both forms of youth disengagement. </p> Discussion <p>This study underscores the need for purposeful interventions to support youths’ social and academic well-being in the post-pandemic era, especially in light of increasing digital media consumption.</p>