Qualitative studies with young people have shown that wellbeing is something that is felt and sensed in their everyday lives, especially in less formal leisure-time contexts. This article contributes to the current state of research by analyzing the relations between wellbeing and the conditions in young people’s leisure time using a longitudinal, quantitative approach. The analyses are based on a new measurement instrument, which captures conditions in young people’s leisure time in terms of the extent to which they facilitate correspondence and experimentation, and require adaption. The measurement instrument was inserted twice (2020, 2022) in the quantitative panel of ‘Pathways to the Future’, a project about young people in Vienna. The analytical sample consists of 239 panel participants (478 observations), and the main results are based on the specification of a random effects model. The findings reveal that possibilities for correspondence in the panel participants’ leisure time, i.e., being able to be oneself and to relax, increase their wellbeing. In addition, to a lesser extent, possibilities for experimentation, i.e., discovering new traits about oneself and engaging in stimulating activities, are important for wellbeing. Interestingly, leisure time requiring adaption is not significantly related to wellbeing. More detailed analyses considering decreases and increases of adaption separately by estimating asymmetric effects suggest that adaption can be constraining but can also be more positively connotated. Overall, the results contribute to a relational and situational understanding of wellbeing in quantitative research, which places the focus on the conditions in young people’s everyday life.