A significant part of Department of the Army's (D.A.) efforts overseas involve training local security forces and providing humanitarian assistance. To successfully accomplish these missions, Soldiers and D.A. civilians often need to communicate directly with the host national population, which may require bridging large cultural gaps in understanding. Social Perspective Taking (SPT) is an interpersonal process, which can facilitate these communication challenges. Accurate SPT enables an individual to understand how a situation appears to another person and how that person is reacting to the situation in question while minimizing cultural bias and erroneous assumptions. Failures to attempt engaging in SPT and inaccurate inferences often strain relationships and spark conflict, especially in cross-cultural situations. eCrossCulture, Harvard University, and the U.S Army Research Institute for Behavioral and Social Sciences (ARI) have examined the SPT propensity and SPT abilities of 116 participants in an effort to gauge their preparation for engaging in cross-cultural situations. This paper describes the results of three studies (N=116) conducted with U.S. Army Soldiers and D.A. civilians using pre and post test data from an evaluation of an interactive multimedia SPT curriculum. The results suggest that Soldiers and D.A. civilians with greater maturity and cross-cultural exposure (as reflected by rank and number of deployments) tend to engage in SPT more frequently, and generate more hypothetical explanations of others' behavior. These associations may reflect a more complex understanding of others, which develops from exposure to others in cross-cultural situations, and allows one to be open to varying viewpoints, behaviors and cognitions. These findings are also congruent with the possibility that SPT may be enhanced through exposure and therefore may be trainable.