Objective: To assess social lifestyle, risk-taking behavior, and psychopathology in young adults born very preterm or with a very low birthweight. Study design: This study was part of the 19-year follow-up in a large ongoing collaborative study in the Netherlands (the POPS study) on the long-term outcome of prematurity and dysmaturity. 656 adolescents from the POPS study without serious handicap were compared with peers in the general population in lifestyle, risk-taking behavior, psychopathology, and social participation. Results: Adolescents from the POPS study smoked significantly less than their peers. Compared with their peers, boys from the POPS study consumed alcohol less often, and girls from the POPS study consumed alcohol approximately as often. Lifetime drug-use was significantly lower than in the reference group. With the exception of fare-dodging, criminal behavior in POPS adolescents was significantly lower than in control subjects. Boys had more trouble in establishing a relationship. The clinical psychopathology reported by POPS subjects was not significantly higher than in control subjects. Conclusion: Adolescents born very preterm or with a very low birthweight without serious disabilities engaged less in risk-taking behavior, did not show more psychopathology, but had more difficulties in establishing social contacts. The latter might be attributable to a more prominent internalizing behavior. © 2008 Mosby, Inc. All rights reserved.