The innovations of digital photography are transforming people’s experiences of producing, manipulating, sharing, and using their personal photographic images. The essentialist and representational dualistic viewpoints of photography that were initially developed in the era of the Daguerreotype appear no longer tenable in the contemporary photography era. This study focuses on the ever-changing role of personal photographic images in the three typical photography events, i.e., the selfie production and manipulation, the real-time beautified video sharing on the social media, and the production of deepfake AI face-swaps. The study is inspired by the Deleuze-Guattari concepts and defines personal photographic images as both an assemblage and a constitutive part of the larger assemblages, i.e., the personal photograph production and usage events. Thus, the study proposes the research questions: What are the material and expressive components that compose the different sizes of assemblages? What are the emergent properties and capacities in the different sizes of assemblages? How is the presumed objectivity/reality of personal photographic images deterritorialized and reterritorialized by different digital photography apps? How does the personal photographic image perform as a source of limitations and opportunities for individuals to deal with personal identity, time, and space and to generate new experiences of life? The tetravalent model of assemblages is used as a major analysis toolkit to achieve the research purpose. The thorough analysis and discussion shows the material and expressive components that compose the assemblages and the emergent capacities. It also discloses how the selfieing, face beautifying, and face-swapping apps function as a line of flight to de/re-territorialize the presumed representational association between individuals and their photographic images. The images have become one of the multiplicities or becoming of individuals, either interacting with individuals, acting on individuals, or extending individuals’ disembodied experiences. This study seeks to develop a new theoretical approach to understand the role of personal photographs in our daily life and the rhizomatic experiences that they generate.