I "broke up" with a friend of over 20 years as he seems to be "losing it", and I'm not sure if I did the right thing.

I (40m) ended a 26 year friendship with someone (40m) I've known since high school. I have very mixed feelings about this, and although I don't have a specific question I'm hoping for some feedback. This is going to be a long post. Sorry.

When I started high school I was the new kid in town. We moved to the town where my mom grew up after my parents divorced and my mom decided to go back to college. We moved in with my grandparents, which was a place I had spent quite a bit of time as a child. Having been there every Christmas and nearly every summer vacation I had a couple of friends in the neighborhood, so I wasn't entirely friendless when school started. I also quickly became friends with a guy in my art class who played D&D and invited me to play. That's how I met Gary (not his real name). He was our DM and he was incredibly smart, funny, mean spirited, arrogant, and a bit of a pervert. In other words, the perfect Dungeon Master. I liked him right away.

Gary was always extremely judgmental of everyone and couldn't seem to maintain relationships for very long as no on could ever meet his expectations. As an example, he developed an absolute hatred of one of our good friends because he didn't like that the girls he dated tended to be on the heavier side. Over the years people began to question me as to why I was still friends with him, but I always defended him and stuck by him. Sure he was mean but that was also part of what made him so funny and he always cracked me up whenever we hung out together.

When we went off to college I went to a local state school and he went to a fairly prestigious university in another state. We always kept in touch and I considered him to be one of my best friends, even as our paths diverged. He studied law and became an attorney, I studied art and became a tattooist. He loved sports cars, I rode Harleys. Through all the years we maintained a great friendship, but it wasn't always easy. In our 20s and into our 30s I worked as bouncer in various bars in the evenings and worked as a tattoo artist during the day. As such, I was well known and quite liked in the bar scene and could get into any show I wanted, bartenders would buy me drinks, and people in general knew me and treated me well. Gary was a bit amazed by this and really enjoyed coming to visit and getting the VIP treatment, but his judgmental attitude and arrogance caused a lot of people to dislike him and they would ask me why I was friends with him. I would just say that we were old friends and once you get to know him he's a great guy.

Gary decided that he wanted to buy a tattoo shop with me. I made it clear that I didn't think that I was cut out to be a business man, but if he wanted to do the back office clerical work I would manage the shop and we could split the profits 50/50. This arrangement didn't go as smoothly as planned. Right after we bought the shop he decided that he no longer wanted to practice law and quit the firm where he had only recently become partner to work as a delivery driver. His midlife crisis was exaggerating the worst aspects of his personality. Whenever Gary would come to visit he would say things to our female artists and even female clients that bordered on sexual harassment, to the point where I would have to escort him away from the premises. He also tended to make really nasty remarks about people's tattoos, particularly if they were in places where they were not easily covered like hands or necks. He was just being brutally judgmental and mean to everyone for no good reason. Our artists hated him and no one wanted to come in to work if he was going to be there.

By this time I had gotten married and my wife and I had bought a little 3 acre farm in the country. I no longer went to bars, I would come home right after work and get up at 6 am to do chores. When you've spent over a decade dealing with drunks and fights every night, there is something particularly delightful about growing a nice perfectly ripe tomato. Unfortunately this meant an end to Gary's VIP treatment downtown. I think that and the growing alienation at the shop as well as the general downward spiral he was in made him want out. He told me that he was done and wanted to sell his ownership in the company. I offered to buy him out over time, but he demanded that he wanted a lump sum. Having recently purchased property, I wasn't in a position to borrow more money so I brought it up to my former apprentice who was able to get the financing. I asked Gary if he would help me with the back office stuff, as none of that was familiar to me and he agreed. Our deal was that I would continue to give him any tattoos he wanted if he would continue to help me learn to do the books and file reports with the state, etc. Needless to say, he never did anything to help me take over his former role in the company, a role I knew from the beginning that I was ill suited for and would be tedious to learn.

It was a difficult process to disentangle him from the business as he had opened most of our accounts in his name. Many of those accounts were understanding when I explained the situation to them, that Gary is no longer with the company and I need to be made the primary account holder. There were however 2 accounts that I was unable to alter. One was a lease for office equipment, the other was our business line of credit. I asked him repeatedly to remove himself from those 2 accounts.

That was 8 months ago. About 3 weeks ago Gary texted to say that he was removing himself from our credit account and to watch for a letter that I would need to sign and return in order to finally take ownership of the account. I was quite pleased that this matter would finally be settled and looked forward to signing the letter. Unfortunately the letter never came. Just the other day I was at the bank to do a deposit and asked for my credit statement as I hadn't received it in the mail and wanted to make a payment. I was told that the account had been closed. I was worried because we have a couple of automatic payments that come out of that account and I didn't want to miss a payment. I was also concerned about closing an account with a standing balance as this is terrible for my credit rating. I was told that in order to maintain the account Gary would have to reopen it, stating that it had been closed accidentally, then he could remove himself from the account. I emailed him that information and he responded with a message that took me completely by surprise:

"I’m not going to reopen the credit card account. With all due respect, you’ve known about this since last August, and thus you’ve had eight and a half months to take care of it. I’ve also asked you to make the account change a number of times. The last time I texted you was almost a month ago. How long did you expect me to wait? How many more times was I going to have to pester you about this?  Also, why should I be the one to fix it?  We're at this point because of you, not me.  As for your automatic payments, that’s not my problem. You put them on the card and then failed to change the account name.  Your responsibility, your problem.  I'm done dealing with this, and I'm done contending with your negligence."

At first I thought that he was joking, or that he was losing his mind. I'm the one who has been pestering him to make the changes to the account. I've tried to put the account in my name and I couldn't because he was the account holder and it could only be done by him. It could literally ONLY be done by HIM! To be told that it was my negligence infuriated me. I emailed him back that our association had come to an end and that I never wanted to see or speak to him again.

I have never ended a friendship before. I've drifted apart from friends or just lost interest and stopped talking to them, but I've never "broken up" with a friend. It feels strange, he's a toxic asshole and I'm sure not having him in my life will relieve me of some anxiety, but I worry that he is in a downward spiral that is self destructive and I know I'm one of very few people (like, literally his parents, me, one other friend who uses him for money, and his World of Warcraft guild) who care about him. I'm not sure if ending the friendship was the right thing to do.

TL/DR: Lifelong friendship sours amidst one friends midlife crisis downward spiral. Not sure if I did the right thing.

Submitted April 27, 2019 at 08:27AM by AnotherShipToaster http://bit.ly/2VuUY3g