Pastor John is proud of Stephen ...yet that does not diminish his concern for Stephen's happiness.  He feels Stephen is being held back by unresolved emotions. Pastor John knows how much Stephen loves him as a dad...yet, there is a strong feeling that runs deep within the soul of Stephen that brings with it an empty longing.  It is a big part of who Stephen is; who Stephen has been ...and Stephen is not the type of person who can readily dismiss those sort of feelings. Pastor John challenges Stephen to revisit those feelings ...to not merely dismiss them.  He tells Stephen to fly to Michigan.