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With its bias towards structural factors in explaining political outcomes, International Relations has for long failed to make sense of what leaders make of their personal interactions at summit meetings and other diplomatic venues. In the past decade, a number of scholars (Holmes, Yarh-Milo, Wheeler, Wong, etc.) have theorized how such interactions enable the communication of intentions, with insights borrowed from germane research in cognitive and social psychology, linguistics and microsociology. However, as Holmes and Wheeler (2020, 142) point out recently, this literature has suffered from a “positivity bias”. Face-to-face diplomacy does not always lead to the normative desirable outcome of greater understanding. Leaders may update their beliefs about each other’s intentions, but they can be wrong (Shifrinson 2016; Grynaviski 2010). In other words, misunderstanding rather than understanding ensues. In this paper, I discuss the individual psychological traits, preconceptions that leaders have of each other, and linguistic and microsociological dynamics, that predispose an interaction towards one way or the other. Empirically, I illustrate my argument with a number of anecdotes of face-to-face diplomacy from recent history.