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This photowork presents extracts from a conversation between myself and Andrew Fisher, discussing two interconnected bodies of work: Counterfactual Departures (Bangkok Winter Gardens) (2023) and The Mute (2025). Both series use generative imaging platforms, Midjourney and ChatGPT as a form of speculative imaging practice. Counterfactual Departures is a series of synthetic images reimagining my Thai mother’s migration from Bangkok to Sydney as an event undocumented in photographs, drawing on prompts that capture a fragmented migration story with images that fails to fill a familial archive. The Mute expands from this personal specificity to the broader historical context of Thai women’s migration during the late 1960s and 1970s, drawing on archival resources. The dialogue examines the implications of using generative imaging as a technology of memory within the limitations of statistical aggregation and ethical safeguards set by imaging platforms. Our conversation considers the limitations of prompting historical trauma and its erasure or replacement while covering creative strategies used in both of the works. This includes a reflection of the way style, whether documentary or staged photography, functions as a referent in generative systems, determining the visualization of historical subjects, along with synthetic imaging’s speculative ‘what-could-have-been’ as a structure for collapsing personal and collective histories. We foreground how the qualities of AI imagery become part of an aesthetic strategy to consider the collapsing of cultural, historical, and personal narratives in datasets and the enduring influence of photographic conventions on how bodies, especially women’s bodies, are represented when mediated by generative AI.