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Scholars increasingly emphasize personal biographic characteristics of leaders in explaining patterns of foreign policy behavior. This paper extends insights from this agenda to study how (dis)similarities in the background characteristics of leaders shape outcomes at the dyadic level. Trust and uncertainty are central to explaining conflict via their connections to commitment- and information-related causes of war. We hypothesize that leaders who share more similar backgrounds and life experiences form stronger social bonds and are more trusting of one another. As such, leaders who have more in common with one another should be able to better manage diplomatic disputes and avoid conflict. We test this hypothesis using a new measure of dyadic-leader-level similarity created with the Leader Experience and Attribute Descriptions (LEAD) data set and data on international conflict onset at the dyadic level for all dyads throughout the period of 1946-2004. We find that pairs of leaders with more similar backgrounds are significantly less likely to experience militarized interstate disputes at all levels of hostility even after accounting for a variety of observed and unobservable determinants of conflict.