Affective Diary is a digital diary that makes use of bio-sensors to add some reminiscence of bodily experiences. The design process behind Affective Diary aimed was ‘sensitive’ to three design qualities extracted from a previous project; providing cues of emotional expressivity building on familiarity, making the design open for personal expressivity and be aware of contradictions between modalities. Through the design process of Affective Diary, with frequent user involvements during the process, these design qualities became further tested, developed and refined. By providing a fairly detailed and reflected description of the design process behind Affective Diary, we aim to provide other designers with inspiration on several levels: both in terms of methods used, but also in why these three design qualities are important and how to realize them. Our aim is also to provide designers with knowledge in the form that makes sense to designers: the practical link between design qualities and final results.