It may not be connected, but today the same thing happened to me.
This morning I had a fully functioning Ruby 2.3.1. In my case, Ruby was compiled and installed using ruby-build and is managed by rbenv.
At some point, I updated Homebrew with
brew cleanup --prune=30 brew update brew upgrade
One of the improved formulas was readline 7.0:
$ brew info readline ... /usr/local/Cellar/readline/7.0 (45 files, 2M) Poured from bottle on 2016-10-05 at 08:09:22
Soon afterword, I discovered that my readline support for Ruby was completely broken. I saw errors similar to yours:
/Users/mbrictson/.rbenv/versions/2.3.1/lib/ruby/gems/2.3.0/gems/pry-0.10.4/lib/pry/config/default.rb:151:in `require': dlopen(/Users/mbrictson/.rbenv/versions/2.3.1/lib/ruby/2.3.0/x86_64-darwin15/readline.bundle, 9): Library not loaded: /usr/local/opt/readline/lib/libreadline.6.dylib (LoadError) Referenced from: /Users/mbrictson/.rbenv/versions/2.3.1/lib/ruby/2.3.0/x86_64-darwin15/readline.bundle Reason: image not found - /Users/mbrictson/.rbenv/versions/2.3.1/lib/ruby/2.3.0/x86_64-darwin15/readline.bundle from /Users/mbrictson/.rbenv/versions/2.3.1/lib/ruby/gems/2.3.0/gems/pry-0.10.4/lib/pry/config/default.rb:151:in `lazy_readline'
The solution was to completely remove my Ruby installation and recompile it:
rm -rf ~/.rbenv/versions/2.3.1 rbenv install 2.3.1
I know that you are using rvm, not rbenv, but perhaps the solution in your case is similar: remove your Ruby installation and reinstall it with rvm.
Matt brictson
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