A wealth of evidence suggests that social relationships and social interactions are more satisfying when partners accurately understand one another’s true thoughts and feelings. However, most research on interpersonal understanding (empathic accuracy) has focused on profiling the most effective perceiver, with very little work on how targets contribute to a perceiver’s empathic ability and resulting interaction outcomes. Targets want to be understood, but how do their own cognitive biases and behavioral responses help or hinder this process? Research on the illusion of transparency shows that people tend to overestimate how easily others can detect their innermost thoughts and feelings. Critically, perceived transparency can result in adverse social outcomes (e.g., lower perceptions of social support, feelings of rejection), suggesting that targets can sometimes undermine other people’s ability to understand them and respond to their needs. To investigate this idea, my dissertation included two experimental laboratory studies designed to test the hypothesis that when targets overestimate the transparency of their own feelings, they are less effective at conveying their needs. In turn, perceivers should be less accurate at inferring the targets’ thoughts and feelings, thereby hindering perceivers’ ability to provide effective social support. In Study 1, I manipulated perceived transparency and measured expressiveness during a disclosure task. In Study 2, I manipulated perceived transparency among romantic couples and created an opportunity for targets to seek and receive support from their partners. Study 1 findings reveal that the manipulation consistently increased expressiveness rather than decreased it, and Study 2 showed few significant differences by condition. The findings are discussed in terms of methodological and conceptual difficulties I encountered in empirically distinguishing perceived transparency from expressiveness.