The practice of initiating conversations with “guess what” questions is common across various social settings. This study examines whether askers and guessers share similar desires for correct guesses during these interactions, a question previously unexplored in behavioral sciences. Across five studies, our research uncovered a significant discrepancy: Askers generally exhibited a lower desire for correct guesses compared to guessers. This pattern holds true across diverse social contexts. Moreover, the results of guesses impact the outcomes of conversations, with askers experiencing more enjoyment and being more willing to continue the conversation when guesses are incorrect, whereas guessers have the opposite experience. Further, while individuals may recognize this disparity, adopting a perspective-taking approach does not alter the guesser's desire to guess correctly; however, guessers do decrease that desire when reminded to protect the asker's emotions.