While interest pursuits are widely recognized as being inherently contextual, what this contextuality entails for different interests has not been explored systematically. In this study, 410 adolescents reported on the temporal, epistemic, material, geographical, social, institutional, and cultural dimensions of 820 interest pursuits. Latent class analyses identified four interest pursuit configurations, revealing quantitative (overall high/low structure) and qualitative (expertise- and social-oriented) differences. We observed similar interests being pursued in the same configuration, but also identified individual differences, reflecting the social-historical meaning and object characteristics of interests, as well as adolescents' preferences and structural opportunities. The findings show that interest entails more than a preference for an object, but also a preference for a wider configuration, which should be considered when designing (educational) contexts to stimulate adolescents' interest.