This chapter presents the empirical context, methods, and data from the in-depth semi-structured interviews conducted to explore user-AI interactions. Qualitative data was collected from 20 interviewees with varied shopping behaviors and experiences of AI service usage. Each interview lasted 20–30 minutes and yielded rich insights into key themes such as AI versus human recommendations, AI communication styles, AI humor, and GAI humor. The following sections include the interview purpose and questions, subjects and recruitment methods, data analysis procedures, detailed results, and a comprehensive summary of findings.