The current research used the contexts of U.S. presidential debates and negotiations to examine whether matching the linguistic style of an opponent in a two-party exchange affects the reactions of third-party observers. Building off communication accommodation theory (CAT), interaction alignment theory (IAT), and processing fluency, the authors propose that language style matching (LSM) will improve subsequent third-party evaluations because matching an opponent’s linguistic style reflects greater perspective taking and will make one’s arguments easier to process. In contrast, research on status inferences predicts that LSM will negatively impact third-party evaluations because LSM implies followership. The authors conduct two studies to test these competing hypotheses. Study 1 analyzed transcripts of U.S. presidential debates between 1976 and 2012 and found that candidates who matched their opponent’s linguistic style increased their standing in the polls. Study 2 demonstrated a causal relationship between LSM and third-party observer evaluations using negotiation transcripts.