The social trend is progressively becoming the key feature of current Web understanding (Web 2.0). This trend appears irrepressible as millions of users, directly or indirectly connected through social networks, are able to share and exchange any kind of content, information, feeling or experience. Social interactions radically changed the user approach. Furthermore, the socialization of content around social objects provides new unexplored commercial marketplaces and business opportunities. On the other hand, the progressive evolution of the web towards the Semantic Web (or Web 3.0) provides a formal representation of knowledge based on the meaning of data. When the social meets semantics, the social intelligence can be formed in the context of a semantic environment in which user and community profiles as well as any kind of interaction is semantically represented (Semantic Social Web). This paper first provides a conceptual analysis of the second and third version of the Web model. That discussion is aimed at the definition of a middle concept (Web 2.5) resulting in the convergence and integration of key features from the current and next generation Web. The Semantic Social Web (Web 2.5) has a clear theoretical meaning, understood as the bridge between the overused Web 2.0 and the not yet mature Semantic Web (Web 3.0).