Recent research has suggested that chat-up lines/verbal relationship initiation approaches may act as male sexual displays. But what role does personality play in how individuals rate such approaches? 200 participants (134 females and 66 males) took part in the self-reported, within-subjects design, which involved completing Bale, Morrison & Caryl’s (2005) Chat-up Line Questionnaire, as well as Eysenck’s revised Personality Questionnaire (1994). The research found participants were able to reliably identify what constitutes a successful chat-up line. Approaches that displayed positive character traits, as well as cultural knowledge, were rated the highest. Jokes of a sexual nature and compliments were rated the lowest. Therefore, it was found that Bale et al.’s (2005) findings were replicated, thus providing further support for Miller’s (2000) Mating Mind Hypothesis. However, the results were found to contradict Miller’s (1999) claims regarding humour, as the post-hoc groups of humour and sex-related humour were also low. Other findings from the chat-up line data provided support for two other evolutionary theories: Buss and Schmitt’s (1993) Sexual Strategies Theory and Trivers’ (1972) Parental Investment Theory. With regards to individual personality differences, the present research found evidence that high neuroticism and psychoticism scores can affect how an individual rates particular types of approaches.