A computing device having the capability to dynamically select a voice that will be used by a speech synthesizer in creating synthesized speech for use in communicating with a user of the computing device is provided. For example, in some embodiments, the computing device: i) employs the speech synthesizer to have a first audible communication with the user using a first voice; ii) stores user satisfaction data that can be used to determine a user's satisfaction with an action the user took in response to the first audible communication; and iii) determines whether a different voice should be used during a second audible communication with the user based on the stored user satisfaction data.