**Abstract** \ Many theories of communication claim that perspective-taking is a fundamental component of the successful design of utterances for a specific audience. In three experiments, we investigated perspective-taking in a constrained communication situation: Participants played a word guessing game where each trial required them to select a clue word to communicate a single target word to their partner. In many cases, the task requires participants to take the perspective of their partner when generating, evaluating, and selecting potential clue words. For example, if the target word was ‘heart’, the first word that came to mind might be ‘love’, but this would not in fact be a very useful clue word. Instead, a word like ‘cardiovascular’ is much more likely than ‘love’ to make the partner guess ‘heart’. Pairs of participants took turns giving and receiving clues to guess target words, receiving feedback after each trial. In Experiment 1, participants appeared unable to improve their perspective-taking over repeated interactions, despite a baseline performance that suggested strong perspective-taking abilities. In Experiment 2, which included extensive feedback after each trial and only target words for which good clues existed and which required perspective-taking, some measures of perspective-taking showed modest improvements. In Experiment 3, which was conducted online, we used Experiment 2 feedback with Experiment 1 target words. As in Experiment 1, participants did not improve over the course of the game in Experiment 3. The results of these three experiments show quite strong limits on people’s ability to adapt and improve perspective-taking without the context provided by interaction history and growing common ground.