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There are few experiences as futile a rehashing the same ;canned, superficial questions in hopes of sparking a deeper, more meaningful conversation with someone. Real insight into other people comes from authentic interactions. If your objective is getting to know someone better, it’s important to foster an environment in which you can both feel safe being your true selves during a candid, frank exchange. And while it should be obvious, many of us forget that even the people we’re closest to or super interested in could use an invitation to open up further about themselves from time to time. Here are 20 good questions to ask a guy to get to know him better, whether you’ve just met or if you’re going on your th date. This doesn’t have to be sexual!

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