A possible self is a combination of the self knowledge, thoughts and beliefs that we have regarding our future potential (Markus & Nurius, 1986). This study investigated the possible selves of eight Japanese niversity study abroad (SA) students. Dörnyei (2005) posited the L2 motivational self-system, comprised of the L2 ideal self as a construct for better understanding and predicting L2 motivation. Several studies and theoretical accounts indicate that discrepancies between current and ideal states can help predict motivation, as the possible self acts as a future self-guide (Dörnyei & Chan, 2013; Higgins, 1987; Ushioda & Dörnyei, 2012). The study identified several key contextual elements that contributed to changes in the participants’ L2 motivational self systems. These included ‘thrown in the deep end’ type interactions, good timing of interactions, conscious moves by the conversation partner to assist the participants, relaxed and positive atmosphere, opportunities to initiate and sustain interactions and one on one interactions that were in line with the participants’ own cultural identity. The findings suggest the contextual elements shaped the participants’ L2 ideal and feared self images and contributed to the identification of discrepancies between current and desired states which influenced study behaviours, goals and motivation over time.