New trends in information technology are strongly influencing and shaping the growth of e-learning, and progressively resolving a number of critical issues currently limiting its dissemination to wider populations. The main goal of this chapter is to outline the MySelf Project, which aims to expand the potential of e-learning through the implementation of Affective Computing and training in soft skills. The chapter contents are therefore divided into two main sections: firstly, implementation of affective computing in the Myself project through the design and development of a 3D virtual tutor and research on possible implementations of multimodal recognition of user emotions; secondly, the development of 3D interactive simulations for soft skills training. Each section sets out the state of the art for the areas covered, outlines the Myself project objectives and possible operative applications, describes the work carried out to date, and discusses critical issues, open questions and future directions for the project.