Taking the source material available for the Ostend Company’s eighteenth century maritime trading activities in China and Bengal as a vantage point, this article will explore the potential of this material for writing a comparative history on cultural interaction in the Indian Ocean world. It will compare how agents from this Company engaged in cultural interaction as a prerequisite for further economic interaction. Beyond a colonial or econocentric approach, the paper will assume an anthropological perspective, considering cultural interactions as a performative learning process, revealing how company agents participated in and made sense of foreign customs and policies. By comparing the diaries of a 1723 merchant-diplomat in Bengal, and a 1726 merchant in Canton, it will reveal similarities and differences in learning processes in both maritime trading environments. It will provide a summary of several key focuses supporting a comparative history of cultural interaction, such as performative courtly rituals, the role of informants and information on learning how to interact, and the personal reflections of European merchants. The article also demonstrates the potential for a collaborative approach, through the inclusion of comparison with older Chinese sources, in establishing a longue duréeperspective on specific cultural phenomena as aspects of the learning process, such as the differing significance of clothing, or the ritual use of tea or tobacco in receiving of guests. Its focus on interaction also reveals the mediating role of Persian or Armenian merchants. Finally, the article will also stress the role of unexpected occurrences such as shipwrecks or robbery, as hazardous aspects of maritime trading environments, and the human response to occurrences on both direct and institutional levels. Against an overtly structural approach, this reveals how human-environment interaction also contained an element of unpredictability.