This study examined associations between characteristics of teenagers' relationships with their mothers and their later socializing behavior and peer relationship quality online. At age 13, teenagers and their mothers participated in an interaction in which mothers' and adolescents' behavior undermining autonomy and relatedness was observed and indicators of teens' depressive symptoms and social anxiety were assessed. At age 20, youth self-reported on their online behaviors, youths' social networking webpages were observationally coded to assess peer relationship quality online, and symptoms of depression and social anxiety were reassessed. Results suggested that problematic mother–teen relationships were predictive of youths' later preference for online communication and greater likelihood of forming a friendship with someone met online, yet poorer quality in online relationships. Findings are discussed within a developmental framework suggesting the importance of considering youths' family interactions during early adolescence as predictors of future online socializing behavior and online interactions with peers.