Video calls have become an important tool for families separated by distance, especially during the pandemic when it was for many the only way to see their families. However, video calls don’t fully replicate the experience of in-person meetings. One significant challenge is keeping children engaged during these calls. In this paper, we examine how playful communication technology can strengthen bonds between grandparents and grandchildren. Our study analyzed long-distance relationships and the activities they share. We found that painting and storytelling are promising activities. “Tell Me a Story” is a playful mobile prototype that combines video calls with a shared painting canvas and call recording features. The results showed that while the prototype successfully encouraged shared activities and strengthened bonds, there are areas for improvement, particularly in video call quality and overall user experience for painting.