The HappyUrns project is an applied research and application project with the primary goals of (1) studying people’s difficulty in facing the topic of death and (2) developing approaches to break this taboo and encourage meaningful conversations about end-of-life topics between loved ones and significant others. Based on iterative user studies and design innovation applications, a range of innovative experiences and products were created that allow people to celebrate life with their loved ones while exploring mortality in an open and honest way. Two primary participant groups were engaged as part of this project: residents of nursing homes in Singapore, and a general population in Singapore and other nations representing diversity across age and other demographic factors. Three experience interventions were developed through full implementation and tested with these participant groups: customized urns developed with the elderly or seriously ill, a Life-in-a-Year-Book to encourage meaningful conversations about mortality through journaling and sharing amongst significant others, and a Celebration Kit that includes inspirational prompts suggesting activities that can be done alone or together, map templates to organize these activities into memory lanes so that they can be experiences again even after someone has passed. These intervention designs were iteratively tested over a two-year period with a large sample size of participants. The results were coded using a range of linguistic and semantic representations, resulting in a range of insights. Key findings from the test results demonstrate the potential efficacy and impact such interventions can have on people’s lives as they engage meaningfully with mortality in an open manner. Ultimately, these types of tangible designs enable people to broach the topic of death, provide comfort during difficult times, and create lasting memories that will live on after loved ones have passed away.