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After that first foray into online dating, she later turned to a dating coach and matchmaker, who helped sort potential dates and navigate the sites. People who work with older adults say they are turning more to apps and websites. Match has its own dating site and app for people over 50, called OurTime.

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Start off small: ask a doorman how his day is going, chat with your waitress, or make polite conversation with someone in the elevator. Chicago is filled with endless options ranging from co-ed sports like beach volleyball , dodgeball , and kickball to activities like improv classes at Second City or iO. You may also want sign up for sites like MeetUp. While having the ability to block out the outside world can be convenient in many scenarios, it also makes it incredibly difficult to approach you.

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