Over the last two decades, the world of dating has undergone significant changes, reshaping how people connect and build relationships. Twenty years ago, dating primarily revolved around in-person interactions, with people meeting through mutual friends, social events, or even chance encounters. The idea of online dating was still in its infancy, and traditional courtship was more common, with individuals relying heavily on face-to-face communication and phone calls to develop their connections. Today, the dating landscape is dominated by technology, with apps and social media playing a crucial role in how people meet and interact. The rise of dating apps has not only made it easier to meet new people but also introduced new challenges, such as the overwhelming number of options and the tendency to judge potential partners based on superficial traits. Additionally, social media has blurred the lines between private and public life, making it easier for people to learn about each other before even going on a first date, but also contributing to unrealistic expectations and pressures. These changes have transformed dating from a more personal, intimate experience to one that is highly influenced by technology and social norms. While it has opened up opportunities for people to meet others they might never have encountered otherwise, it has also led to new complexities in forming meaningful relationships. The evolution of dating over the last two decades highlights the impact of technology on human connections and the ongoing shift in how relationships are initiated and maintained.