Online dating can be overwhelming. There is less time being put into crafting meaningful conversations. To solve this problem, I worked with OkCupid to find new playful ways of encouraging people to converse better leading to more in-person dates. Working closely with OkCupid's Engineering Team, we segmented three different user scenarios based on profile data—low, medium and high. Using profile data mining, the app would use machine learning to auto-generate customizable "icebreakers" in playful ways.