Phenotypic plasticity, both within and between generations, allows organisms to respond to a changing world. Here, we aim to investigate how paternal phenotypes interact to shape offspring life-histories, focussing on two ubiquitous animal experiences: ageing and feeding. We present preliminary results from an ongoing experiment using Drosophila melanogaster: a full-factorial design, where fathers were fed one of two diets (control and higher-sucrose) and male and female offspring collected when fathers were young (one week) and old (five weeks). These offspring were then assigned to diets either matching or mismatching those of their fathers, and their survival and weekly reproductive output measured. We find complex interactions between paternal age, paternal diet, and offspring diet shape different aspects of offspring life-history, in a sex-specific manner. This investigation illuminates how organisms cope with environmental variation over their own lifespans and between generations, exploring the myriad forms of information parents transfer to their offspring, and the conditions under which this occurs.