In times of digitalization, analyzing the highly complex media practices and mediated life worlds of individuals has become highly challenging, both in theoretical and methodological terms. From an empirical point of view, diary methods, and particularly qualitative (media) diaries, bear a great potential to gain access to these media practices and analyze them within the contexts of people’s everyday lives. In this article, we propose that it is fruitful to apply the characteristics of real diaries to research settings and consider them when designing diary studies as a researcher. Doing so can help to collect more “genuine” data and get a more holistic and adequate picture of digital media life. These characteristics comprise: (1) authenticity and naturalness, (2) autonomy in design, (3) multimodality and materiality, (4) intrinsic motivation, (5) functionalities of diary keeping, (6) continuity and periodicity, as well as (7) inferences about cultural and social conditions. We provide suggestions for implementing these characteristics in qualitative diary studies, and discuss the empirical challenges accompanying this approach.