Twenty Japanese university freshmen majoring in International Studies (N = 4) and Nursing (N = 16) participated in a 10-month project examining changes in their motivation. Using monthly focus group interviews and a 35-item questionnaire, the dynamic systems of various types of learners of English over two semesters were explored. Trajectories of learners' dynamic systems were studied, adapting Complexity Thought Modeling [Larsen-Freeman, D., and L. Cameron. 2008. "Complex Systems and Applied Linguistics." Oxford: Oxford University Press] and Retrodictive Qualitative Modeling [Dörnyei, Z. 2014. "Researching Complex Dynamic Systems: 'Retrodictive Qualitative Modeling' in the Language Classroom." "Language Teaching" 47/1: 80-91]. First, five learner types were identified using quantitative data. Next, a variety of demotivators and motivators that learners experience both inside and outside of their classrooms were analyzed using the qualitative data obtained from the eight monthly focus group interviews and reflective journal entries. Using the data obtained, this study focused on how five learners' systems and contexts adapt to each other, and how the dynamics of the five learners' system change over two semesters. Each learner was different in their trajectory of motivation and what kinds of attractor states that they experienced. It showed that each type of learner experienced unique motivators and demotivators in/outside of the classroom and reacted differently. In conclusion, it is important to reexamine the contexts of learner demotivation and motivation from a Dynamic Systems perspective.