Anandibai looked at her American penfriends as a source of enlightenment on various subjects earlier outside her ken. But perhaps the openness of these communications, not possible within the rigid and closed relationships within the Indian family, appealed to her. 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 and 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 Kolkata. It is an interesting account of diversity in practices within the Indian social milieu that Anandibai was putting into perspective for friends, and the reaction their own progressive attitudes drew from various factions in the new city.