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This paper presents the main methodological issues met with during the research on adolescent everyday life information behavior in the context of making informed decisions, which was carried out in Croatia from 2018 to 2020. It does not focus on the research results, but rather on the methodological issues and concerns that had occurred stemming from the specific life period of the population being investigated, and on the ways the researchers delt with them. They are offered as potentially useful for consideration to those who will investigate adolescent information behavior in other contexts. Six main methodological dilemmas arose while planning the design of research methodology coming out from six questions: what would be the appropriate research approach and design to investigate adolescent information behavior in the context of making informed everyday life decisions, what would be the developmentally appropriate way to investigate the phenomena, how to gain access to the potential adolescent research participants, how to negotiate an adult researcher's position when interacting with adolescents, how to get adolescent participants' trust needed to collect rich data and what ethical issues need to be considered. We offer an overview of the dilemmas and concerns, as well as the ways they were dealt with, acknowledging the contribution of those scholars who had responded to similar challenges in the past.