Let's talk about S, baby (part 1)

From a reader:

A young man who I consider to be a close friend of mine (as well as an occasional “lover,” if you will) began to - seemingly jokingly - assert that he was a sociopath. I laughed, gave an unserious “right” in response, and thought virtually nothing of the matter until I researched the topic earlier this week on no more than a trivial whim. My preliminary discoveries being what they were, my light-hearted curiosity quickly escalated to full-blown panic. Every piece of his character seemed to fit so perfectly, and every article, blog, and comment seemed to conclude with a “run for your life!” mentality. While alarmed and distressed, I am not a runner, and thankfully continued my investigation until it led me to your blog.

I’ll start with some background information on my friend. He is extremely intelligent, and thinks in ways that frequently cause my mind to ache or attempt to shut down completely. He can memorize entire conversations, scenes, large portions of books, and who knows what else. He is also extremely contradictory. He’ll act as the life of the party or show up at my door every day for a week, then retreat completely to his basement for days or weeks at a time, explaining that he is totally incapable of dealing with people and society. After knowing him for a few months, I toyed with ideas of bipolarity and even Asperger’s, as he mentioned once that he believed his father might suffer from the syndrome. But a year of further interaction and observation later, these explanations just don’t quite cut it. The following are characteristics he has displayed or openly explained to me:

• He claims to hate humanity – or at least humanity as we are now, and will often toy with people, setting up mind games and manipulating people around him in order to observe their responses. He says he no longer believes in truth after witnessing the deceit that man is capable of for personal gain. He’s even said that he thinks we are all sociopaths to some degree. He can charm his way into or out of any situation. He is reckless. He drives too fast, laughs too loud, and eats without tasting. He has told me that he cannot feel and that he does not believe in empathy. He does not cry; he doesn’t get hurt; he doesn’t understand these reactions and emotions.
• He’s asked me on numerous occasions what it feels like to cry. He’s seen me cry on several occasions due to pain he inflicted and admitted that he cannot comprehend why I feel the way I do. He says he cares for people, but not in the same way that everyone else does. He doesn’t miss people. He would not grieve were one of his family members to die.
• He was ostracized in elementary and middle school. He didn’t know how to interact with other children and acted out constantly in school. He deliberately enraged teachers and other authority figures with tricks and mind games. In high school and college, he says he learned how to appropriately interact with others through observation, and engages in interpersonal play out of general interest and necessity.
• He is fascinated by music and film, claiming that these mediums allow him to feel more “real” than real life. Sometimes he believes himself a "real" human; sometimes he does not.
• He’s deeply hurt almost everyone who has been close to him for an extended period of time, and appears to feel no remorse, yet is noticeably distressed at the idea of being seen as a “monster.” When drunk, I have witnessed incredible bouts of rage aimed at the world, himself, and every mailbox in between. He tried to kill himself two years ago, but failed (whether miraculously or intentionally, I’m unsure).

So after all this, my question for you is what can I do? How do I confront him without it coming off as an attack or negative accusation? If he truly is a sociopath, I want him to know that I can accept it, can accept him, and that I will not think of him as a heartless monster; that I will try to understand him as best I can, and believe we both may have something to gain through mutual understanding, respect, and continued exploration.

But I’m afraid that he has observed so much deceit within humans that he simply will not believe me. He won’t trust it. I want him to know that he doesn’t need to play the games or wear the masks with me that he does with everyone else. That if he will communicate his thoughts to me, no matter how far from my own, I will accept them and offer what I can in return. Do you think this is possible?