Experimental research on the effects of cellular phone conversations on driving indicates that the phone task interferes with many driving-related functions, especially with older drivers. Unfortunately in past research (1) the dual task conditions were not repeated in order to test for learning, (2) the 'phone tasks' were not representative of real conversations, and (3) most often both the driving and the phone tasks were experimenter-paced. In real driving drivers learn to time-share various tasks, they can pace their driving to accommodate the demands of a phone conversation, and they can even partially pace the phone conversation to accommodate the driving demands. The present study was designed to better simulate real driving conditions by providing a simulated driving environment with repeated experiences of driving while carrying two different hands-free 'phone' tasks with different proximities to real conversations. In the course of five sessions of driving and using the phone, there was a learning effect on most of the driving measures. In addition, the interference from the phone task on many of the driving tasks diminished over time as expected. Finally, the interference effects were greater when the phone task was the often-used artificial math operations task than when it was an emotionally involving conversation, when the driving demands were greater, and when the drivers were older. Thus, the deleterious effects of conversing on the phone are very real initially, but may not be as severe with continued practice at the dual task, especially for drivers who are not old.