internet revolutionized our lifestyle. New generation devices like smartphones and tablets allow us to be always connected: the web represents a significant part of our days. These epochal changes bring with them questions about the potentialities and the risks of web 2.0. This chapter introduces a research whose purpose is to investigate the relationships between Online and Offline lives in Emerging Adulthood. Starting by the concept of functional organ (Leont'ev, 1972) and inverse instrumentality (Ekbia & Nardi, 2012), the goal of the study is to go beyond the research on web addiction, and start to explore a model able to predict why some emerging adults have their life empowered by the web and while others get trapped in the problematic use.