Disclosed is an information processing apparatus including a reception unit configured to receive a use reservation of car sharing including designation of any one of round-trip car sharing and one-way car sharing, designation of a pickup location, and designation of a drop-off location from a user and store the use reservation in a use reservation database, and a selection unit configured to select, as users who share a ride in a vehicle, both of a first user who has made a use reservation for designating round-trip car sharing and a second user who has made a use reservation for designating one-way car sharing among a plurality of users who have made a use reservation with a pickup location and a drop-off location satisfying a predetermined condition.