I have a long-time friend that I think is insecure, and the insecurity is destroying the friendship. Objectively, he is in a life situation that is much better than mine, so it’s extra confusing. Here are the things I have tried that seem to have made things worse:

• Giving him complements often
• Letting him choose what topics to discuss
• Initiating conversations about him
• Not speaking well of myself and avoiding mention or discussion of any of my accomplishments, no matter how meaningless (e.g. I had fun at an event today, I made a delicious lunch, I mowed the yard, etc.)
• Pointing out my disadvantages, flaws, and failures
• Validating his opinions and stances on debatable topics while restraining my critiques

Despite these accommodations, rather than helping improve the situation, I feel like they are being taken as opportunities to devalue me to address his insecurity. I had no problem taking a hit for a while, but this has been getting worse for at least a year and has gotten to the point that I have to choose to either stop tolerating it or let it affect my dignity. I’m barely allowed to exist anymore. Talking about it directly wont work because he has denied it and even called me “too sensitive” when I pointed out changes in his behavior towards me.

Anyone been in a similar situation? What was going on? What helped? What made things worse?