This qualitative study examines the role of childhood experiences and memories in shaping individuals’ gender identities, expressions, and life trajectories. Whilst some research has examined the role of gender stereotypes in people's life trajectories, no research has focused on people's retrospective accounts of their gender socialisation about their current understanding of (their own) gender. We conducted eight semi-structured interviews with 20–30-year-olds living in the UK to do this. We employed interpretative phenomenological analysis to analyse our data, which enabled us to investigate participants’ memories of their gender socialisations, observations, and internalisations in childhood and their interpretation of these experiences. Using insights from social learning theory, this study provides further insights into the processes of observations, internalisations, and subsequent challenges to gender based on their retrospective accounts. We show the impact of hegemonic gender stereotypes in the participants' life trajectories and hobbies (mainly sports), showing the limitations created by the gender binary system. Notably, the present findings support social learning theory, as it shows how the internalisation of gender can be challenged by new forms of gender resocialisation, including the promotion of gender equity in sports, the possibilities of gender expressions and identities beyond the binary, and the free articulation and expression of these concerns in society. By showing how gender internalisations can be malleable, this research provides practical recommendations for tackling unnecessary gender divisions in childhood settings.