Internet and online-based social systems are rising as the dominant mode of communication in society. However, the public or semi-private environment under which most online communications operate under do not make them suitable channels for speaking with others about personal or emotional problems. This has led to the emergence of online platforms for emotional support offering free, anonymous, and confidential conversations with live listeners. Yet very little is known about the way these platforms are utilized, and if their features and design foster strong user engagement. This paper explores the utilization and the interaction features of hundreds of thousands of users on 7 Cups of Tea, a leading online platform offering online emotional support. It dissects the level of activity of hundreds of thousands of users, the patterns by which they engage in conversation with each other, and uses machine learning methods to find factors promoting engagement. The study may be the first to measure activities and interactions in a large-scale online social system that fosters peer-to-peer emotional support.