[Object] To provide a communication system and a communication control method capable of obtaining reliable feedback from a user further naturally through a conversation with an agent without imposing a burden on the user. [Solution] The communication system includes: a communication unit configured to receive request information for requesting feedback on a specific experience of a user; an accumulation unit configured to accumulate the feedback received from a client terminal of the user via the communication unit; and a control unit configured to perform control such that a question for requesting the feedback on the specific experience of the user based on the request information is transmitted to the client terminal of the user at a timing according to context of the user, and feedback input by the user in response to the question output as speech of an agent via the client terminal is received.