This chapter, with correspondences from the time the couple moved to Kolkata for better prospects, explores the many difficulties they faced in the new city, as well as details Anandibai’s own chronic ill health. While she retells her American penfriends the sentiments that lead her to reject the offer of employment at the postal service, she also details the cultural shock that the Hindu couple had to cope with in Serampore. Religion as a topic for discussion seems to have been broached for the first time. As their socio-cultural orbit slowly expanded, and the couple found themselves more integrated in their new setup, the chapter also explores the first vestiges of Anandibai’s ‘American dream’. In a time when upper-caste women were closely guarded, their bold decision to send her to America for studies was met with shock and awe.