Overtaking maneuvers on two-lane rural roads are difficult maneuvers which involve relatively complicated decisions. The main hypothesis tested in this paper is that the frequency of overtaking maneuvers on a driving simulator is associated with a faulty decision making style in the Iowa Gambling Task (IGT), a popular decision task employed for assessing cognitive impulsivity. In a controlled study, 36 participants drove a scenario involving multiple overtaking decisions in an interactive driving simulator (STISIM) and also completed the IGT. The results show a significant negative correlation of about 0.3 between the IGT performance and the number of overtaking maneuvers, the average driving speed, and the acceleration noise. We also found a positive correlation of 0.5 between IGT performance and the percent of aborted overtaking maneuvers. A cognitive modeling analysis shows that the associations appear to be modulated by weighting of gains compared to losses obtained during repeated play. These results demonstrate that the IGT has a potential to predict risk prone behavior in overtaking maneuvers and in driving in general.