A telephone advertisement system acquires, in response to receiving a telephone talk request from a caller to a callee, callee information indicating a callee from a caller terminal device of the caller. The telephone advertisement system acquires, based on the acquired callee information, advertisement content associated with a condition corresponding to an attribute of the callee among a plurality of pieces of advertisement content, each of the plurality of piece of advertisement content associated with a condition of a person to whom respective advertisement content is presented, the condition of the person stored in a predetermined storage. The telephone advertisement system transmits the acquired advertisement content to the caller terminal device to cause the caller terminal device to present the advertisement content within an invitation period during which the callee is being invited to answer an incoming call.