This photo-video essay is part of an on-going project, “Anita & Ava —Photography as a Self-Restorative Tool”, which looks at how two childhood friends explored their gender identity through photography, as they transitioned into adulthood. Fan Chon originally found this series of photographic portraits in an antique shop in Penang. The portraits were of the late Ava Leong taken in the 1950s and 1960s in which she self-restored from an adolescent boy to a woman. After the artist got in touch with Ava’s surviving lifelong friend, Anita, the collection expanded and he carried out a series of interviews with Anita to gather background information on these photographs. A compilation of Anita’s voices is used as the foundation of this video essay. These audio clips are juxtaposed with a selection from Ava and Anita’s photographic collection that reveals their 70-year friendship, their journey of self-discovery through studio photography and other social activities, Anita’s working experience as a school lab technician and her life onstage as a female impersonator. This work intends to give us a glimpse of a time when they, together with their peers from the transgender community, were allowed to explore their sense of self while contributing to a lively cosmopolitan artistic culture in Malaysia.