The paper presents the design of an end-to-end communication system aimed at enhancing interactions between elderly individuals and their grandchildren, focusing on the use of playful design elements in a structured requirements engineering process. It explores key concepts such as immediacy, emotional expression, and non-synchronicity to create an awareness system that supports ongoing relationships through effortless communication. The methodology employed includes diary studies, field testing with prototypes, and interviews, all aimed at ensuring that the technology aligns with the daily routines and needs of both target user groups.