Disclosed herein is a communication system including: a first apparatus and a second apparatus being communication terminals at least one of which resides on a mobile object; and a server apparatus. The server apparatus includes: a determination block configured to determine whether the first and the second apparatuses are in close proximity to each other based on position data of the first apparatus and on position data of the second apparatus; and a communication block configured such that if the determination block determines that the first and the second apparatuses are in close proximity to each other, the communication block transmits preinstalled content data to at least one of the first and the second apparatuses.