Many who move countries today do so for work, and labour mobility – both temporary and permanent – is the mechanism by which countless people (both movers and stayers) come into contact with cultural difference. The domain of mobile labour is thus an important context through which to consider the transformative possibilities of encounters with racial and cultural difference. Situated within debates on everyday multi-culture and vernacular cosmopolitanisms, this essay considers the question of intercultural encounter at work in relation to the layered histories of race and variegated citizenships of mobile labour in Singapore. Exploring the micro-nature of cosmopolitan practices, the paper considers under what labour conditions might an outward-looking cosmopolitan sensibility and a convivial openness to otherness emerge among migrant workers, as against a set of survival-based intercultural capacities. I reflect specifically upon two cases of ‘incongruous encounter’ in workplaces reliant on precariously employed migrant labour: a mainland Chinese man and a Filipina woman who, because of Singapore’s racialised system of work visas, find themselves working in South Asian restaurants in Singapore’s Little India. They both engage ‘cosmopolitan practices’, yet their sensibilities differ sharply. Their stories highlight how, in a place like Singapore, the ‘encounter’ needs to be understood within a regime of mobile labour, situated racial hierarchies, and a highly stratified system of work visas. I further suggest that situational factors such as the nature of work including its spatial and temporal qualities, the mixture of co-workers, and recognition relations with superiors all mattered in framing the affective atmospheres of encounter. In a context of forced encounter, I argue that learnt capacities to function and interact across difference should not necessarily be romanticised as a cosmopolitan sensibility.