This chapter demonstrates how a reciprocal research and design (RR&D) model is possible and has value in design. The authors see other design-based researchers in the learning sciences relying on basic studies as part of their development projects. The RR&D process had the benefit of creating links between the theory-building work we do in learning research while keeping us involved with and contributing to the lives of families. The authors are pleased that we have been able to engage in a process that enables us to manage professional missions while maintaining the spirit of empathy-driven design processes. The social experiences with math that the chapter uncovered in its initial interview study did not carry forward when families were not setting aside special family time to meet with us. Therefore, this is a cautionary tale for those practicing user-centered design that includes human-computer interface design and field testing.