The purpose of the current study was to examine older adults' preferences for conversational pain management content to incorporate in an interactive application (app) for pain self-management. Conversational statements and questions were written as a script to encourage evidence-based pain self-management behaviors. The content was converted from text to female chatbot speech and saved as four groups of MP3 files. A purposive sample of 22 older adults participated in a guided interaction through the MP3 files. One-on-one interviews were conducted to garner participants' conversational content preferences. Overall, participants want the conversational content to increase health care provider engagement in pain management communication. Older adults preferred the inclusion of conversational statements and questions for monitoring the multifaceted dimensions of pain, treatment accountability, guidance for alternative treatments, and undesirable effects from pain treatments. The design of mobile health apps must incorporate the needs and preferences of older adults. [Journal of Gerontological Nursing, 49(1), 11-17.].