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Across all domains of human social life, positive perceptions of conversational listening (i.e., feeling heard) predict well-being, professional success, and interpersonal flourishing. However, a fundamental question remains: Are perceptions of listening accurate? Prior research has not empirically tested the extent to which humans can detect others’ cognitive engagement (attentiveness) during live conversation. Across five studies (total N = 1,225), using a combination of correlational and experimental methods, we find that perceivers struggle to distinguish between attentive and inattentive conversational listening. Though people’s listening fluctuated naturally throughout their conversations (people’s minds wandered away from the conversation 24% of the time), they were able to adjust their listening in line with instructions and incentives—by either listening attentively, inattentively, or dividing their attention—and their conversation partners struggled to detect these differences. Specifically, speakers consistently overestimated their conversation partners’ attentiveness—often believing their partners were listening when they were not. Our results suggest this overestimation is (at least partly) due to the largely indistinguishable behavior of inattentive and attentive listeners. It appears that people can (and do) divide their attention during conversation and successfully feign attentiveness. Overestimating others’ attentiveness extended to third-party observers who were not immersed in the conversation, listeners who looked back on their own listening, and people interacting with partners who could not hear their words (but were incentivized to act like they could). Our work calls for a reexamination of a fundamental social behavior—listening—and underscores the distinction between feeling heard and being heard during live conversation.