The choice of a friendly interface for learning a foreign language is the fundamental theme of the research illustrated in this paper. Several are the means used in a dialogue among human beings and they essentially require the knowledge of the linguistic terminology, the context where the dialogue is inserted and the final goal. The use of technological tools which emulate the human beings’ manners can be useful in the communication processes where the interaction with situations of the every-day life is required. HyperEnglish, the multimedia courseware we are developing, is a prototype for the experimentation and evaluation of the reached hypotheses, where the fundamental goal is the building of an intelligent environment to learn the English language simplifying the communication and allowing to live emotions of the real life.