Research has indicated that online daters may pick up on language cues connected to personality traits in online dating profile texts, and act upon those cues. This research seeks to investigate the level of accuracy of detection of personality in dating profile texts, and the extent to which perceived or actual similarity of personality has an effect on attractiveness of the author. An online survey was conducted collecting the Ten Item Personality Inventory (TIPI) for each participant and text author, a peer-report TIPI score by participants for each text author, and an attractiveness rating on a Likert scale for each author. Participants correctly identified Extraversion, though the effect size was small. Contrary to the hypotheses, participants preferred texts when written by an author with a personality they perceived as dissimilar to their own, specifically in Openness and Conscientiousness, and no relationship was found between actual similarity of personality and attractiveness. Online daters may choose partners with complementary or desirable traits rather than similar traits, or other factors in attraction may be more salient in the initial stages of determining attraction.