The first year of university can be a vulnerable time, especially for students who describe themselves as shy and who may be reluctant to engage socially. Shyness, which can be closely aligned with social anxiety, often reduces opportunities for students to belong. This paper presents the experiences of two students negotiating experiences of shyness and belonging during their first year at university. Scholars have focused on how young people "negotiate" belonging(s) in multiple spaces. These negotiations provide insights into complex, varied and multi-faceted relationships which contribute to the lives of young people and which are integral to their identity development. The paper foregrounds four common trends in scholarship on belonging (space/place, memory/nostalgia, temporality and relationships) to structure the analysis of positionality, shyness and intersubjectivity during a transitional time. How both these students "come to belong" in reference to everyday social practices complicates a psychological or disability-studies approach to the study of shyness and provides insight into the realities of student experience, personal hardship and familial responsibility.