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The struggle – and bright side – of online dating for people. And it's not just happening in Chicago – online dating is a practice that is becoming increasingly popular all over America. It’s quite clear, for singles, Chicago is a city with a thriving social life, come day or night, there is always an exciting club, bar or live music event to attend. Feb 13, 2018 Chicago writer Dustin Seibert, 36, penned a comprehensive review of dating apps for the website Very Smart Brothas. He met his ex-wife online and continues to use apps to connect with women.