Following Johanna Hedva’s ‘Sick Woman Theory’ (2016/2022), this co-authored, epistolary essay theorizes and practises the letter-like ‘flight’ as an affective, attentive writerly form and intimate historical encounter, which makes possible new readings – speculative, slow, suspended – of the careworn lives, works, and representations of two ‘sick women’ subjects: Liliana Amon (writer, actress, portrait sitter, 1892–1939) and Cookie Mueller (writer, actress, portrait sitter, 1949–1989). Through a series of flights exchanged – which evolve across non-linear, murmuring timelines; projections through the air, eye, mind; through time and space – we bring archival research on and with Amon and Mueller’s sickened lives, works, and materials into cross-historical correspondence, tracing scenes and relations across the medical and non-medical that are both care-less and full-of-care. This is proposed as a queer-feminist research method that draws its reparative effects from looking, waiting and writing. In correspondence with our subjects’ own living, making and writing of belatedness, our flights seek to register and revitalize the possibilities of temporally deviant care – beside mothering beside sickness beside writing. In our shared flights, we dare to look at them as the mother and not-quite mother; to wait with them and the pressure-points for thought that they pose; and to do so in the endurance, remembrance, belatedness and ongoing goodbyes of our writing-as-flight, which in turn revitalizes the complexities of our sick women subjects’ creativities and cares.