Most people experience their first romantic relationship during adolescence. However, there is also a substantial proportion of youth who remain single during this time. Delaying the transition into the first romantic relationship may be associated with a decrease in self-esteem which might recover or even increase after youth engage in their first romantic relationship. The current study examined self-esteem development surrounding the transition into the first romantic relationship over a period of 10 years in a sample of N = 1395 adolescents (Mage = 16.22 at T1; Mage = 26.22 at T11) from pairfam, a German representative panel study starting in 2008. Results from multilevel piecewise growth curve models showed that self-esteem did not change before beginning the first relationship, but slightly decreased thereafter. There were no moderating effects of age at first relationship, single satisfaction, or relationship satisfaction. However, both single and partnered youth who were more satisfied with their current relationship status reported higher self-esteem on average. Overall, the findings extend the current understanding of self-esteem development surrounding the transition into the first romantic relationship. Being single during late adolescence and emerging adulthood does not seem to pose a risk for youth’s self-esteem development.