This study examined how emoticons influence the perception of messages in computer-mediated communication. 77 participants engaged in an online chat about a dry campus policy and then rated their conversation partner. Results showed that those who were less emotionally stable and more agreeable were more likely to use emoticons. Participants perceived chat partners using positive emoticons with optimistic messages as more agreeable. A wink emoticon led to higher perceived extraversion ratings. The study provides insight into how personality and emoticons can affect impressions during online conversations.