This study aims to gain insight into attitudes toward dating in modern Japan. Apart from regular relationships, casual dating and casual relationships without the intention to marry have become more common. Therefore, this study was conducted to find out the attitude toward dating, casual dating, and the intention to marry. One of the purposes of the study was also to gain knowledge of possible issues in the modern dating world, such as whether dating applications (e.g., Tinder and Omiai) have made a difference in the world of dating. A case study was conducted by doing three individual semi-structured interviews with three Japanese young adults born between the years 1993-2003 which were then analyzed and compared. The results suggest that casual dating has indeed become more common, but it may have a stigma around it. Common themes such as couples not having enough time together, money and dating apps were discussed as possible issues. Marriage intentions were found to be slightly different among the respondents and age could be one of the factors for that.