This paper discusses our vision of the future with respect to the introduction of virtual assistants in the e-market. It presents the latest evolution of the involvement framework, an on-going model aimed at driving the design and the evaluation of social agents virtual characters designed to set up lasting relationships with the users. The framework is based on a review of the literature and on the systematic analysis of the first generation social agents available on the Web. Moreover, it is enriched by empirical results of two user-based evaluations of Granny, a social agent that tries to inject a specific personality into the interaction between a financial service provider and a customer. The assumption behind our research is that social agents require a reexamination of the traditional HCI approach to system design and evaluation. Both the usability framework and the media equation paradigm need to be updated to account for the peculiarity of the new interaction form.