During the pandemic, online courses became the major delivery format for most institutions of higher learning across the United States and around the world. However, many students experienced emotional distress as a result and have struggled to adapt to remote learning. To explore how emotional distress relatesto other aspects of online learning, including online learning readiness and academic outcome, we asked a sample of 80 college students to participate in an online survey in the fall semester of 2020. Two distinct online learning readiness patterns were found using k-means cluster analysis. Online learning-ready learners showed statistically significant differences from the not-ready online learners on anxiety, boredom, and satisfaction. Moreover, a three-path mediation model based on a theoretical relationship between online learning readiness, emotional state, and expectation of learning outcome was tested using structural equation modeling (SEM). Results showed that readiness positively predicted satisfaction; furthermore, only satisfaction predicted learning expectation and expected grade. The implications of these findings and limitations of the study are discussed.