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In addition to arranging dates, Stef coaches her clients on how to become more confident and capable daters both offline and online. In the last year, Stef has adapted to the fast-changing dating scene by offering online dating assistance to clients seeking quality dates. His bad experience made him leery of trusting another dating professional with his love life. Stef and the City is a traditional matchmaking company founded by Chicago dating expert Stef Safran. She listened to his problems and gave him practical dating advice based on her experience as CEO of Stef and the City , a Chicago-based matchmaking firm.