Evaluating Privacy & Security of Online Dating Applications with a Focus on Older Adults examines how dating apps collect, store, and share personal data, and how secure and trustworthy interactions are supported across platforms. The topic covers authentication, profile management, messaging, contact discovery, and geo-location features, with particular attention to the needs and vulnerabilities of older users. It considers how privacy and security concerns can influence user trust, autonomy, and safety in intimate online contexts, and how design choices and governance practices shape the overall risk landscape. Evaluation approaches discussed include threat modeling, privacy impact considerations, and security testing across the app stack—from client interfaces to server-side data handling and third-party integrations. Emphasis is placed on data minimization, transparent data use, consent management, and robust authentication and session controls. The focus on older adults invites examination of usability and accessibility of privacy notices, as well as the interaction between user behavior, risk perception, and protective measures. The workshop may consider regulatory and governance aspects, including privacy standards and data-sharing agreements, to frame evaluation criteria and compliance considerations. Expected outcomes include guidance for developers, researchers, and policymakers on designing and assessing dating apps that better protect privacy and security for older users. The material aims to outline practical design patterns, evaluation metrics, and risk-mitigation strategies that balance ease of use with protection. By identifying common gaps and sharing best practices, the discussion contributes to safer, more inclusive online dating experiences and informs ongoing work in privacy engineering, human-computer interaction, and security research.