How do people find answers to questions they encounter in everyday life? While extensive research has examined how people go about finding answers to questions online, there has been little work investigating the issue from a more holistic, in situ perspective that covers the various devices, resources, and contextual factors that influence everyday question-asking experiences. To address this, we developed a text-messaging-based data-collection framework. This paper details our approach including reflections on both the benefits and challenges of the methodology for researchers seeking to apply similar approaches to social science research. In doing so, we demonstrate how our methodology helps establish a contextually rich understanding of information-seeking processes. We also demonstrate our approach to analyzing data from a small but diverse group of adults across the United States about their everyday question-asking experiences.