Concerns have been raised about how viewing Sexually Explicit Internet Material (SEIM) shapes adolescents' understanding of sexual relationships and has potentially negative impacts. However, research frequently takes a narrow view of adolescent SEIM use and excludes their understandings. The present study explored how 13 participants, aged 14 to 15 years, made sense of their experiences with SEIM. In-depth individual interviews were conducted, and five dominant dilemmas faced by participants were abstracted using interpretive analysis. We discuss how these dilemmas were negotiated by adolescents using various strategies. The analysis provides new understandings of how adolescents interpret their SEIM experiences and highlights the limitations of understanding SEIM use solely through risk models. On a practical level, these findings can inform youth, parents and caregivers, and professionals as to how they might understand and help young people navigate the complex area of SEIM.