The author discusses how contact is resisted, broken, and restored in his work with three men: one who is seriously and destructively paranoid, another locked in an obsessive compulsive way of being, and a third in the grip of schizoid withdrawal that has obstructed his life. The paper describes the author's attempt to navigate through each man's resistance to contact, as well as his own countertransference resistances, which are both inevitable and necessary. The inherent pleasure, as well as the pain and peril embedded in those resistances, are examined.