Researchers have suggested that experimentation may be a necessary, constructive component of identity formation. However, these researchers have also noted the paradox of risk taking; an individual may experience both positive and negative precursors and consequences of risk taking. The present investigation used qualitative methods to explore the personal meaning of experimentation behaviors and of this paradox to college students. A stratified sample of 12 community college students (6 female) and 20 university students (10 female) was interviewed. Data were analyzed using grounded theory methods. Students described a deliberate and functional process of experimenting with a variety of risk behaviors. This included articulating the ways in which the college culture promotes participation in risk behaviors as developmentally appropriate experimentation.