For many years, upward state social comparison has been one of the most popular mechanisms explaining why social media use negatively affects psychological well-being. More recent research has challenged this, showing that different types of upward state social comparison on social media could affect psychological well-being positively or negatively. Despite all these findings, existing research has multiple problems in measuring upward state social comparison. In addition, few studies clearly identify what factors could influence an individual to engage in different types of upward state social comparison on social media, which in turn affect psychological well-being positively or negatively. To address these research limitations, three studies are conducted in this dissertation. Study1, a critical review paper, reviews the literature on social media use, upward state social comparison, and psychological well-being, and discusses multiple measurement issues and a research gap in this body of research. Then, study2, addressing the measurement problems discussed in study1, develops a new measurement scale of assimilative and contrastive upward state social comparison; in addition, addressing the research gap identified in study1, study2 also tests the relationships between passive social media use, trait self-compassion, different motivations of upward social comparison, different types of upward state social comparison, and psychological well-being. Then, study3 is an experimental study that tests the causal links between different motivations of upward social comparison and different types of upward state social comparison. In general, this dissertation addresses multiple measurement issues and a research gap related to upward state social comparison on social media, enriching the theoretical understandings of the research field of social media use, upward state social comparison, and psychological well-being.