The continuous furtherance of technology has paved new ways of information creation and retrieval. Web 2.0 has enabled simple users to overpass the limitations of geographical, ethnical, ethical and economical boundaries and become active creators, elaborators and assessors of information. User-Generated Content (UGC) shared over the Internet on a daily basis has surpassed every expectation and surmise. Having the biggest knowledge database (the Web) within their grasp, learners are learning at a faster pace than they used to and become quickly familiar with the most recent findings and innovations. The emergence and increased popularity of social media further contribute to these new trends of informal types of knowledge sharing and learning. Such types of online social interactions and user-generated data exchanges are felt by many as more familiar, more personal, free, friendlier, and in some cases even more understandable. Recognizing the impact that social media and UGC exchanges have had on creating new more engaging, more natural and more motivating ways of online learning, the paper presents a well-thought methodology for dynamically discovering content, shared within social media communities, of significant educational value to be retrieved as learning resources in specific learning contexts.