Charles & I (62 GWM), friends since 8th grade, I worked in tech, and he had a small business. Increasingly over time, Charles struggles with rage. Since his mom died in 2020, he’s been in “reset mode.” He burnt through his inheritance, a house sale, and a lottery win. He won’t even toast a bagel or make a cup of coffee, high-end everything. He burns bridges. He cohabited a house when the co-owner abandoned it, got a restraining order, and a legal remedy to divest from it. He is living off credit cards. Last year, a friend gave him a job. He clashed with everyone, complained to his boss friend about everything, and from what he says, the ending was reality housewives TV worthy. In 2021, a mutual friend offered me a job. Charles was incensed that she hadn’t offered him a job; then he looked up the job salary and told me I was entitled. He blocked her. When they were visiting our hometown holidays, he caused a public scene when she asked why he had blocked her. I’ve always tried to be supportive without being judgmental. Our conversations have gotten difficult. If I ask how his new profession is going, he snaps that not everyone gets offered a free job. If I share something I’m doing in retirement, the response is, “Must be nice. I can’t afford that. You live in a different reality.” It’s become harder to discuss anything without him becoming resentful. He is now a TikToker; it’s all political Angertainment about the right. I’ve had some serious health issues the last five years (2 cancers, heart, liver, pancreas problems, UC). My prescriptions are $60k/yr before insurance. So when my COBRA ended and I had to switch to ACA, my premiums doubled. We were talking about Social Security when I told Charles that my entire check basically goes toward health insurance, I’m looking forward to Medicare. He said, “Well, I guess you just won’t be Mr. Globe Trotter anymore. You’ll have to sit at home and live off scraps and Netflix like us peasants.” I said, “Yeah, guess I’ll just have to give up my shopping and Amazon addiction and no Starbucks.” He said I was an A-hole for talking about having to pay for insurance when he doesn’t have the money to pay for insurance. I was entitled, compared me to people he hates, said I don’t know what the real world is like, and told me to go F myself. He even threw in a homophobic slur and accused me of secretly being a Republican, to which I know I threw gas on and said maybe I am. He hung up, blocked me everywhere, and that was that. I’m not surprised based on history. I know he struggles, and I understand it must be hard to hear about someone else’s retirement when he feels left behind. But I was just being honest about my own fears, not bragging, not rubbing it in. We’ve been friends for 45 years, and I thought I could talk openly about my health and money worries. So… AITA for sharing my retirement and health concerns with a friend who is in a worse financial spot?