Distance separated grandparents and grandchildren often face challenges in staying connected. To explore this topic, we designed G2G, a shared calendar and video messaging system to connect young children (ages 5-10) with their grandparents over distance. Our design focused on providing grandparents and grandchildren with an awareness of each other's lives to support conversations and design elements to help reduce the need for parent scaffolding. A field study with two grandparent-grandchild pairs over two months showed that systems designed around structured communication can help young children develop a routine around staying in touch with their remote grandparents. Autonomy in maintaining awareness can help children to be engaged more easily. This suggests that designs focusing on connecting young children to their grandparents over distance should be flexible yet structured and designing to reduce parental scaffolding can lead to positive effects and strengthened relationships.