In an example system, an information processing apparatus is caused to function as a user image acquisition unit which acquires a user image captured by using a camera of a portable information processing apparatus, a communication partner image acquisition unit which acquires a communication partner image via a network, and a display control unit which causes the user image to be displayed on at least one of a display of the portable information processing apparatus and an external display, and which causes the communication partner image to be displayed on at least one of the display of the portable information processing apparatus and the external display.