Brett Stokar

Brett Stokar is the founder of Approach Connections, a Chicago-based dating app designed to bring back real-life connections in a world dominated by swiping and endless messaging. With a background in startups and business development, Brett saw firsthand how technology could be leveraged to solve real-world problems—but also how it could create barriers to authentic human interaction. This led him to develop Approach, a platform that helps singles meet naturally by matching only when they are checked into the same physical location, such as a bar, event, or social space.

Through his work, Brett has studied how modern dating culture has become more transactional and detached, leading many singles to feel frustrated with traditional apps. Instead of swiping endlessly on people they may never meet, users of Approach are given real opportunities to connect in the moment, reducing ghosting, mismatched expectations, and digital fatigue.

With years of experience launching and scaling early-stage startups, Brett has a deep understanding of consumer behavior, social dynamics, and how technology can be used to foster meaningful, in-person relationships. He is passionate about rethinking modern dating norms and helping people rediscover the ease and excitement of meeting organically.

When he’s not working on Approach (IRL), Brett enjoys spending time with his family and playing chess, a game that, much like dating, requires strategy, patience, and knowing when to make the right move.