During the COVID-19 pandemic lockdowns (2020-2021), almost all facets of life were rendered digital – health, work, schooling, and logistics. In this phenomenon, not only did digital access become synonymous with social inclusion but inequalities were also amplified – particularly in the case of older adults (65 years and over). Contemporary older adults represent one of the most diverse spectrums of digital media users – spanning from technologically savvy to non-users. As the first generation of older adults to age in and through data in a data-saturated world, their understandings and experiences can teach us much about the possibilities and limitations of new media. Understanding these practices through cultural probes – like drawing, photos and writing prompts – can enable playful behaviours that not only elicit new thoughts and actions but also allow insight into some of the tacit lived experience that can support opportunities for technological use. In this paper, we ask: How can we playfully co-design through personas to enhance understandings of older adults’ lived experience of digital media? In this paper, we focus on the six co-design workshops in which we deployed personas as representations of digital experience to challenge, explore, provoke and help build nuanced tools for implementation. Through personas, speculative fiction and lived experience collide, offering some fascinating ways to rethink the digital-social dimension for older adults now and into the future.