The challenges impacting the distribution of contextual media are privacy and fragmentation. These factors could hamper the evolution of the social web and ultimately new media consumption. Regardless, the growth in niche content in a long-tailed Internet requires more effective methods of delivering media. The growth of social networks constitutes and endorses the suggestion of the social web. This scheme could utilize current data models that would allow specific content to be retrieved, tailored to the user. The complexity of these data structures requires aggregated semantics and metadata to consolidate information and define ties between the user and a resource or object. The value proposition to users is that their leveraged personal information will enable the retrieval of r fofelevant media. The governance of personal information is entrusted into the social network, which is another obstacle in this newly defined paradigm. The distribution channels will influence the new media era, which will involve enhancing retrieval and consumption and reshape production and application. The migration of users to social networking sites will consequently lead this social web evolution. The fulfillment of the social web requires continual monitoring and observation studies to review the feasibility and ensure that objectives are consistently user focused. As famous American inventor, Charles F Kettering said, “I am interested in the future because I am going to spend the rest of my life there”.