Diary studies require participants to record entries at the moment of events, but the process often distracts the participants and disrupts the flow of the events. In this work, we explore the notion of delayed reflection for diary studies. Users quickly denote cues of diary events and only reflect on the cues later when they are not busy. To minimize disruptions, we employed a squeeze gesture that is swift and discreet for denoting cues. We investigated the feasibility of delayed reflection and compared it against a conventional digital diary that requires users to reflect immediately at the time of entry. In a weeklong field study, we asked participants to record their daily experiences with both types of diaries. Our results show that users’ preference is context-dependent. Delayed reflection is favored for use in contexts when interruptions are deemed inappropriate (e.g. in meetings or lectures) or when the users are mobile (e.g. walking). In contrast, the users prefer immediate reflection when they are alone, such as during leisure and downtime.