Romantic relationships represents a central aspect of adolescents’ lives. Although there has been a growing recognition of the developmental importance of these relationships in theory, it is only in recent decades that substantial attention has been given to romantic relationships during adolescence. As a result, numerous aspects regarding the dynamics of romantic relationship (in)experiences remain unknown. The current dissertation aimed to fill this gap by providing a detailed understanding of these dynamics during the transition from adolescence to emerging adulthood. Three studies were conducted using data from a large and representative sample in Germany. The interdisciplinary approach allowed for a comprehensive investigation of romantic relationship (in)experiences from different perspectives, including differential, developmental, and sociological viewpoints.