A learning content mentoring system for use by a user to master a desired dialog stream includes a computer operable to run an editor program and generate a scenario file including a plurality of scenario segments of the desired dialog, and a player interface configured to electronically communicate with the scenario file. In this regard, the editor program is operable to challenge the user with the scenario segments of the desired dialog, the player interface is operable to transmit a response from the user to the editor program for comparison with an expected response, and the editor program interacts with the player interface based on the user response to train the user to respond with the desired dialog.