There is an increasing interest in exploiting social media data to address problems in various domains, including social science and psychology. Reddit is a well-known social media platform that promotes user interactions on various topics and accumulates massive amounts of data daily. Reddit users participate in discussions by posting reddits, which could be text posts, links, images, and videos, or by reacting to reddits via up- or down-votes. These reddits can be analyzed to investigate mass opinion on particular issues. In this thesis, we analyze users' behavioral trends and morals of expiry dating using reddits. A relationship can start from casual dating and may not come with future bonding; such a relationship starts with an expiration date, which is known at the initial stage. People tend to seek advice on this type of relationship on social media, including Reddit. In this study, we extract reddits on relationships and apply machine-learning-based methods to infer trends on expiry dating. We adapt anchor-based topic models to infer topics from reddit corpus and estimate the trends over these topics. In addition, we infer the moral intentions--care/harm, fairness/cheating, purity/degradation, authority/subversion, loyalty/betrayed--of individuals while getting into expiry relationships based on the updated moral foundation theory framework. We collected ~665K reddits under various subreddits from 2019 to 2022. Our analysis shows an increasing trend in the topic 'dating with end date' where the moral is 'fairness' over these years.