This paper reports on the research results regarding children's positioning in their daydreaming narratives. A special feature of the research was its cross-generational character, i.e. we have collected and analyzed written accounts of primary school children's daydreams in grade 4, which were produced in the year 1984 and the year 2009. One of the major insights from our research is that children's daydreaming narratives broadly belong to the category of 'preferred self' constructions. We classified these preferred self-constructions in three categories, namely 'fictional selves', 'future selves' and 'actual selves', which emerged from repetitive themes in children's narratives. Each of these broad categories was further 'unpacked' into more specific constructions of preferred selves. Based on the qualitative data we developed hypotheses about generational shifts in preferred self constructions and used nonparametric statistical tests to evaluate these hypotheses.