An information processing apparatus according to an aspect of the present invention includes a situation specifying unit configured to specify a part of a situation of the measurement subject on the basis of the number of measurements of the biological information in each situation of the measurement subject at the time of measuring biological information of the measurement subject by a biological information measuring unit, a current situation detecting unit configured to detect a current situation of the measurement subject, and a support information output unit configured to output support information relating to measurement of the biological information if the current situation corresponds to the measurement promoting situation.