Provided is an anonymous communication system that allows an originator to determine the anonymous characteristics of communicating parties when communication is established. Disclosed is an anonymous communication system and an anonymous communication establishing apparatus to be installed in an anonymous communication system that are characterized enabling a communication by anonymity, said anonymous communication system detecting anonymities of communication parties when establishing a communication session, and notifying them to a communication device of a caller. Disclosed is an anonymous communication method that is enabling a communication by anonymity, said anonymous communication method detecting anonymities of communication parties when establishing a communication session, and notifying them to a communication device of a caller.