Relationship marketing (RM) is about retaining customers through the achievement of long-term mutual satisfaction by businesses and their customers. Sport organizations, to retain customers by establishing, maintaining, and enhancing relationships, need to communicate and engage in dialogue with their customers. To achieve this on an ongoing basis, sport organizations need to employ effective communication platforms. In this regard, social media (SM) is becoming an ideal tool for a continuing 2-way dialogue. However, the effects of SM, primarily in terms of addressing RM goals, are not yet well understood. This study explores the opportunities and challenges facing managers in sport organizations in using SM in an RM strategy. Eight case studies were undertaken on organizations that put on running events. The article presents the findings on the use, opportunities, and challenges of SM and recommendations encouraging continued investigation.