An object of the present disclosure is to provide a technology that makes it possible that a plurality of users use a vehicle that does not have a specified regular driver. An information processing apparatus determines whether or not after a first user moves to a destination place by driving a first vehicle, a second user is able to move by driving the first vehicle from the destination place ofthe first user as a departure place. If an affirmative determination is made in the determining, the information processing apparatus matches the first user and the second user with the first vehicle.