We explore the role of digital media in supporting intergenerational interactions between people with dementia and young people. Though meaningful social interaction is integral to quality of life in dementia, initiating conversation with a person with dementia can be challenging, especially for younger people who may lack knowledge of someone's life history. This can be further compounded without a nuanced understanding of the nature of dementia, along with an unfamiliarity in leading and maintaining conversation. We designed a mobile application-Ticket to Talk-to support intergenerational interactions by encouraging young people to collect media relevant to individuals with dementia to use in conversations with people with dementia. We evaluated Ticket to Talk through trials with two families, a care home, and groups of older people. We highlight difficulties in using technologies such as this as a conversational tool, the value of digital media in supporting intergenerational interactions, and the potential to positively shape people with dementia's agency in social settings.