This study is an attempt to understand the plight of paid Filipino male live-in caregivers in Toronto. Caregiving has historically been associated with women. Today, live-in caregiving is normalised as Filipino women’s work. Cultures, language and policies promote this gendering. What happens when a Filipino man decides to undertake paid live-in caregiving? This study wants to understand the trajectories that surround caregiving and masculinity; particularly looking at paid Filipino immigrant man. By invoking trans-nationality and border crossing, this study lays bare issues of masculinity and paid caregiving in Toronto.