Definition: Given a real-life anecdote of a complex ethical situation, generate a suitable title that describes the main event/root cause of the situation. Imagine that the given text is a social media post, and you have to write the title of the post, so the users can decide to read the main text or not.
Input: Sorry for the long post I am trying to include as much relevant information as I can. 

Let's get a couple of statements out of the way. 

1. I am a pretty blunt person, very type A, and am often considered the asshole. 
2. I only care about what other people think of me to the extent that I use it as a self modifying tool (if I am the asshole I then identify what it is that I need to adjust in myself)
3. I am constantly working on bettering myself for others for myself (see statement 2). I know this does not excuse any behaviors I do, but it explains why I am here asking about this. 

It is possible he might find this post as he does sometimes browse reddit but I doubt it since he's not really aware of this sub. But if he does I hope he knows I am asking because of genuine care for him and our friendship. 

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Let's get down the the question. I have noticed over the several years we have been friends that my friend (let's call him George) has some peculiarities that could put him as very high functioning Aspergers. I majored in a branch of psychology which was not enough to by any means diagnose him, but enough that I notice some tendencies and know that since George is so high functioning a diagnosis could have been missed or overlooked. Most of his "quirks" are acceptable and do not hinder our friendship or his social interaction in general. He understands that sometime things are  considered inappropriate in general social situations, but does not really know what those are specifically, so he just goes into "safe mode" where he doesn't say anything controversial at all, even to those he considers friends. I do not think this is by any means a bad thing, but it means he is uncomfortable opening up to us and therefore limits our friendship. I do not say this because I am assuming I say it because after several years of friendship with George he expressed to a mutual friend that he is afraid that I will "be done with him" and then he will lose all his friends because of it. Let me explain this statement. I run a meetup group where most of our interactions and socializing are done through there or with the "core" people and those that have been removed from the meetup group are usually no longer invited to things that are off meetup. I then had a discussion with George about how I hope he trusts the strength of our friendship enough that he can talk to me about things that bother him, concern him, or he is wary about and he, by the end of it, agreed that he felt he could. 

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Last night we were playing a game and as I was setting up the arena he kept running over the traps I placed consuming them before their intended purpose. This in itself is not a problem or even a deal let alone big deal or small deal. But it is a habit of his. When Diablo 2 was a thing, one of his self proclaimed favorite things was to min/max a character, join a group of hardcore characters (when you die you lose everything, even the character) and help them quest and such and then drop a bunch hydras (stationary "pets" that do damage for you), port back to town, and then enable PVP having the hydras kill the whole party and everyone loses all their things and their characters become unplayable. Again, it's a game so it's not like people's lives were ruined or anything but people still put considerable amount of time and effort into leveling these characters. He did it just to have them lose everything, he did not gain experience, loot, or anything else from them dying. A second example is how a friend just discovered an elephant sanctuary that was taking volunteers. Let's call this friend Jane. Jane was never going to go to this sanctuary as she could not afford to stop work to volunteer all her time. This was very clear, even to George. Regardless, he spent about 10 minutes going back and forth with Jane about how "you'll just be shoveling poop. It's not like they're just going to let you play with the elephants" to which Jane would tell George "I know that, but like, why do you have to ruin my nice fantasy?". 

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So last night when he did the very very minor running over my traps just to waste them because he knew that I only had a limited amount of them I made a comment/question of "why do you do that? Does it make you feel nice to ruin things for people or do you get some sort of something else out of it?" to which re flippantly replied "yes, clearly I just like to ruin peoples lives because I'm just evil". So, a non-answer. 

My question is this: would I be the asshole to press him again today about it? I don't really think this behavior is so bad that it would really interfere with our friendship (or if it did, would be very minimal) but I also want to address a thing that I see as unhelpful in his learning to better interact with friends and strangers. Also, it irritates me a little bit. But the big ass caveat is, that is not my place to make him address a thing that he does not want to address himself. He did not come to me asking me for help, so WIBTA for offering this advice anyway? 

talking to my friend about the fact that he likes to "ruin peoples good time"