Social Web platforms are quickly becoming the natural place for people to engage in discussing current events, topics, and policies. Analysing such discussions is of high value to analysts who are interested in assessing up-to-the-minute public opinion, consensus, and trends. However, we have a limited understanding of how content and user features can influence the amount of response that posts (e.g., Twitter messages) receive, and how this can impact the growth of discussion threads. Understanding these dynamics can help users to issue better posts, and enable analysts to make timely predictions on which discussion threads will evolve into active ones and which are likely to wither too quickly. In this paper we present an approach for predicting discussions on the Social Web, by (a) identifying seed posts, then (b) making predictions on the level of discussion that such posts will generate. We explore the use of post-content and user features and their subsequent effects on predictions. Our experiments produced an optimum F1 score of 0.848 for identifying seed posts, and an average measure of 0.673 for Normalised Discounted Cumulative Gain when predicting discussion levels.