Indian matrimonial portals have worked around a communication model that involves elders at every stage of discussion to ensure that the seriousness of the subject is maintained. Hence, the majority of such portal users are parents or family members. The entire process right from creating profile of prospective brides or grooms to searching desired prospects till marriage sounds straightforward however it actually is not. This project revolves around identifying such challenges that users encounter during conversations with interested profiles and proposes a solution that would help users in overcoming them. The project was carried out in phases that involved desk research, user interactions, analysis, concept explorations and feedbacks on proposed solution.