As text-messaging chatbots become increasingly “human”, it will be important to understand the personal interactions that users are seeking with a chatbot. What chatbot personalities are most compelling to young, urban users in India? To explore this question, we conducted Wizard-of-Oz (WoZ) studies with users that simulated interactions with a hypothetical chatbot. Participants were told that there might be a human involved in the chat, although the extent to which the human would be involved was not revealed. We synthesize the results into a set of recommendations for future chatbots.