People may want deep and meaningful relationships with others, but may also be reluctant to engage in the deep and meaningful conversations with strangers that could create those relationships. We hypothesized that people systematically underestimate how caring and interested distant strangers are in one's own intimate revelations and that these miscalibrated expectations create a psychological barrier to deeper conversations. As predicted, conversations between strangers felt less awkward, and created more connectedness and happiness, than the participants themselves expected (Experiments 1a-5). Participants were especially prone to overestimate how awkward deep conversations would be compared with shallow conversations (Experiments 2-5). Notably, they also felt more connected to deep conversation partners than shallow conversation partners after having both types of conversations (Experiments 6a-b). Systematic differences between expectations and experiences arose because participants expected others to care less about their disclosures in conversation than others actually did (Experiments 1a, 1b, 4a, 4b, 5, and 6a). As a result, participants more accurately predicted the outcomes of their conversations when speaking with close friends, family, or partners whose care and interest is more clearly known (Experiment 5). Miscalibrated expectations about others matter because they guide decisions about which topics to discuss in conversation, such that more calibrated expectations encourage deeper conversation (Experiments 7a-7b). Misunderstanding others can encourage overly shallow interactions. (PsycInfo Database Record (c) 2022 APA, all rights reserved).