AI-powered dating tools are rapidly transforming how people connect, flirt, and form relationships online - creating unprecedented challenges for dating safety and authenticity. This session explores how AI wingmen, dating coaches, and dating app features can be used both legitimately and maliciously in modern dating. We'll examine the benefits of these technologies - and downsides, including how they can accelerate intimacy, manipulate emotions, and create false connections, while providing practical strategies for safely navigating AI-enhanced interactions.