Natural language generation has been one of the prime focuses of human-AI collaboration in recent years. We are specifically interested in exploring the idea of creativity in human-AI co-creation, most especially in the context of persona generation for the iterativehuman-centered design process. Collaborating with AIs to generate engaging personas may present opportunities to overcome the shortcomings of personas and how they’re currently used in the design process. We aim to study how collaborating with AIs might help designers and researchers to create engaging personas and narrative scenarios for their products, and by extension the implications of human-AI collaborative creative writing on fields like literature with character generation. The implications of such a study could be generalized beyond user-experience design and persona generation. The ability to create engaging personas is not dissimilar from the ability to generate characters as a whole, and the subsequent potential for natural language generation to assist in creative writing and thinking is implicit. In this paper, we will discuss the process and potential merits of iterating with AIs for creative content creation, as well as expand upon experiments we have conducted and the questions we hope to answer in our future research.