A few years ago, this friend and I drove eight hours to another state to shoot his friend's wedding (we were videography partners). Dude was already a pretty big fuckup as a business partner (had us lose jobs, never did any work, always relied on me to finish stuff and contact clients, etc) and an asshole, I just was a wuss and gave him the benefit of the doubt because we had known eachother so long.
The day of the wedding comes and I find out we've been fired because, get this, my friend hadn't contacted the groom at all after the hiring, and hadn't ever finished the engagement video he shot for them, so the groom decided fuck it and hired someone else. This friend then tells me, to cover the cost of the $100 plane ticket out of there (we drove there, I was gonna fly out the next day while he stayed), that he will pay me that money if I edit another months-overdue video for him for a client who was just too nice to fire him. I do it, he wires me the money, then yells at me later after spying on me while I talk on the phone with my girlfriend (I told her everything). "You seem bitter," he exclaims, "but this is way worse for me. Just understand that, you have no reason to be mad". Of course, you know, I had only broken even on my plane ticket. That doesn't count the fact that I took off work, had to pay for all my food here, and lost out on the money I would've made from the wedding gig. The dude never admitted fault in this whole issue.
I held my cool cos I needed a ride to the airport. A few days later he got angry at me because I didn't want to party with him on the 4th of July, instead I wanted to work a video gig shooting a concert. I told him politely that it was going against my better judgement to be around him. I wish I just told him to fuck off and that I'm certain he's a sociopath and should get help. In retrospect I saw all of this shitstorm coming, but did nothing about it so I had to make a change
Mutual friends are telling me that he has just gotten weirder and weirder, to the point where many think he is either developing schizophrenia or is getting really bad at hiding his obvious psychopathy.