<p>Online daters use a variety of messages to initiate relationships, some of which contain sexual content. Research has explored some extreme versions of initiation messages that contain sexual content that are used in online dating. However, there has been a lack of examination into the variation in these types of initiation strategies. The current study explored different types of initiation messages that contain sexual content used in online dating and recipients’ impressions of those messages. The first study utilized focus groups to uncover the different types of initiation messages that contain sexual content that online daters have sent and received, as well as their perceptions of those messages. The second study employed findings from Study 1 to develop and validate the impressions of initiation messages that contain sexual content (IIMCSC) scale and conduct an exploratory correlation analysis on how factors from the IIMCSC scale relate to relational outcomes. The development of a typology of initiation messages that contain sexual content along with the IIMCSC scale to measure recipients’ impressions of those messages are useful in understanding how these messages play a role in the initiation of romantic relationships. The developed tools address the need for more comprehensive understanding and investigation of the variety of sexual content exchanged in online romantic relationship initiation. </p>