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Authentic Relating: Relational Risk and Reward

Whether it's walking past strangers or staying in the bounds of familiar conversation, what has us choose to lean towards the unknown or lean back in the safety of what's most understood and known?  

If you had more options on the menu to create connection and meaningful conversation, would you try them out?  How would you?  Why would you?  What's the point and purpose?  What might happen?