As new technologies emerge that can bring older adults together with children, little has been discussed by researchers concerning the design methods used to create these new technologies. Giving both children and older adults a voice in a shared design process comes with many challenges. This paper details an exploratory study focusing on connecting generations through cooperative design (co-design) methods that can enable idea construction and elaboration to flourish. Design techniques were adapted that ranged from low-tech prototyping and sticky-note feedback to distributed collaboration. The critical finding in this research was that children and older adults need not only time together to start the collaboration but also time apart to further the collaboration at a distance. This case study research reports on how our methods evolved and how others can apply these methods for their own work. (Contains 2 tables and 7 figures.)