Matchup had long been a successful matchmaking club for the religious Jewish community based on one key principle, helping your friends find love. When the company decided to turn this model into a mobile app the challenge was to preserve its unique interpersonal logic while making the process engaging intuitive and culturally respectful. Unlike swipe based dating apps Matchup requires users to fill out detailed profiles about their single friends and answer multiple guided questions. My task was to design a user flow and interface that made this process fun motivating and easy to complete. By integrating playful illustrated questions and personalized interactions the app turns a long profile survey into a dynamic and entertaining journey. Each question is paired with a unique illustration creating a sense of progress and anticipation. The flow between the four users involved, you, your friend, the other matchmaker and their friend, was carefully mapped to maintain clarity and momentum. We also designed an intuitive in app chat for essential communication steps. The result is a culturally tailored product that blends tradition with digital convenience and actually makes people smile while filling out profiles.