Online venues present both risks and opportunities for youth, and research suggests that some youth may be more susceptible to the risks while others are more likely to take advantage of the opportunities. In this chapter, we adopt a developmental framework to describe the current state of knowledge regarding the negative effects and benefits of youths’ online behaviour as well as the positive effects of online interactions. Most importantly, we tease apart the potential individual characteristics that may indicate which adolescents are at risk versus those who may benefit from online interactions. As we show in this chapter, the assessment of “user” and “usage” characteristics may enhance our understanding of the nuanced relation between digital peer communication and well-being.