Victor Hung, Miguel Elvir, Avelino Gonzalez, Ronald DeMara Intelligent Systems Laboratory University of Central Florida Orlando, FL USA victor@isl.ucf.edu, miguel.elvir@isl.ucf.edu, gonzalez@ucf.edu, demara@mail.ucf.edu "Towards a Method For Evaluating Naturalness in Conversational Dialog Systems" IEEE International Conference on Systems, Man, and Cybernetics, San Antonio, Texas, October, 2009. The evaluation of conversational dialog systems has always remained a controversial topic, as it is unclear on how to quantitatively describe how well a conversation agent performs, or how much better one is over another. Furthermore, one of the hurdles in this quandary remains the definition of naturalness, as in how well a dialog system can maintain a natural conversation flow. This paper surveys existing evaluation practices and provides its own methodology to determine the effectiveness and naturalness of a dialog system. A prototype evaluation methodology for the LifeLike virtual avatar project is presented.