An information processing apparatus includes a history acquisition section configured to acquire history data including a history indicating that a plurality of selection subjects have selected selection objects; a learning processing section configured to allow a choice model to learn a preference of each selection subject for a feature and an environmental dependence of selection of each selection object in each selection environment using the history data, where the choice model uses a feature value possessed by each selection object, the preference of each selection subject for the feature, and the environmental dependence indicative of ease of selection of each selection object in each of a plurality of selection environments to calculate a selectability with which each of the plurality of selection subjects selects each selection object; and an output section configured to output results of learning by the learning processing section.