I just discovered I can no longer gem push … any more and some digging led me to a need to update my RVM SSL certs.
I ran rvm osx-ssl-certs status
All the versions of rubies were working for me and I got a project on ruby 2.6.5. then I got this library not found error for openssl. To solve that, I did
brew update
brew upgrade
brew install openssl
Then all the other versions stop working because it library not found for open ssl. Since I am using chruby for ruby version manager, I remove the version folder and reinstall them and it works.
Tl;dr update and upgrade brew, install openssl and reinstall ruby version