There are concerns that social media (SM) use and SM stress may disrupt sleep. However, evidence on both the cross-sectional and longitudinal relationships is limited. Therefore, the main aim of this study is to address this gap in the literature by examining the cross-sectional and longitudinal relationships between SM use, SM stress, and sleep (i.e., sleep latency and daytime sleepiness) in adolescents. In total, 1,441 adolescents 11–15 years, 51% boys) filled out a survey in at least one of three waves that were three to four months apart (NWave1 = 1,241; NWave2 = 1,216; NWave3 = 1,103). Cross-sectionally, we found that SM use and SM stress were positively related to sleep latency and daytime sleepiness. However, when examined together, SM use was not a significant predictor of sleep latency and daytime sleepiness above the effects of SM stress. The longitudinal findings showed that SM stress was positively related to subsequent sleep latency and daytime sleepiness, but only among girls. Our findings stress that it is important to focus on how adolescents perceive and cope with their SM use, instead of focusing on the mere frequency of SM use.