Disclosed herein is an information processing apparatus including an evaluation information extraction section configured to extract evaluation information including an object targeted to be evaluated and an evaluation of the object targeted to be evaluated from a linguistic expression given as information expressed linguistically by a user of interest; an identification section configured to identify whether the evaluation information is of a first type regarding content or of a second type regarding another user; and an evaluation prediction section configured to predict the evaluation by the user of interest regarding the content, based on the evaluation information of the first type given by the user of interest and on the evaluation information given by the other user in the evaluation information of the second type given by the user of interest.