The present study used quantitative and qualitative methods to investigate contextual factors and motivations associated with emerging adults’ electronic aggression victimization and perpetration with friends and dating partners. Participants (N = 226) reported online about electronic aggression occurrence and motivations, family risk, support from friends, and emotion regulation. Males reported more victimization than perpetration overall, whereas females reported more victimization than perpetration only with friends. Jealousy/insecurity emerged as the most common motivation for electronic perpetration; second most common was humor for males and negative emotion for females. Overall, risky family environment was associated with electronic aggression; yet, support from friends and emotion regulation each moderated this association. Discussion addresses potential miscommunications that can occur in electronic communication and the need to look at the interplay between in-person and online interactions.