With the experiment that we outline in this paper, we have had the ambition to pave the way for addressing the problem of supporting, enhancing and measuring collective AND informal learning, in particular serendipity. We want to support a new type of free navigation on Web resources (Documents, Topics, Events and Agents – human and artificial -) that is driven by the learner's current needs and the preferences of the community of trust chosen by the learner, not by external actors. The experiment exploits the ViewpointS Web Application (VWA) prototype, that restructures a private version of a subset of the Web according to personalized choices in order to determine distances/proximities among resources. The process allows to enable, empower and measure the influence of members of the community of trust of the learner, on the learner's choices when navigating in search of THE resources corresponding to THE immediate need, goal, strategy, wish. In the following, we will outline: 1. the rationale of our efforts and 2. the user's reactions during the phase of -formal and informal- learning the functions and use of the prototypical software environment VWA, i.e.: a proof of concept for VWA.