An encouraging speech system includes: at least one of reaction detection means for detecting a user's reaction in response to an encouraging speech and evaluation acquisition means for acquiring an evaluation by an evaluator on a timing and a content of the encouraging speech; good/bad determination means for determining whether the timing and the content of the encouraging speech are good or not based on at least one of the detected reaction and the acquired evaluation; learning means for learning learning data in which the timing and the content of the encouraging speech determined to be good by the good/bad determination means are associated with trigger information which serves as a trigger when this encouraging speech is made; and encouraging speech means for making the encouraging speech based on the trigger information by the user and the results of the learning by the learning means.