Library not loaded: /opt/local/lib/libssl.1.0.0.dylib (LoadError)

Uninstalling openssl and re-installing it worked for me.

brew remove openssl  

and then

brew install openssl

Your questions mentions three paths /opt/local, /usr/local and /etc/openssl they belong to Macports, Homebrew and SM Framework respectively.

As the last one is used to build static rubies it is harmeless and not related to the problem. The other two suggest that you have switched from macports to homebrew between installing the rubies.

You need to reinstall ruby-2.0.0-p195 which is referring still the old paths from macports, you can do it with:

rvm reinstall ruby-2.0.0-p195

You can get more details about the rubies and openssl paths they use running:

rvm --debug osx-ssl-certs update all

Trying to run 'bundle' I also started getting the openssl dylib complaint, though a slightly different path.I tried most of these, and a few other things. I had rvm, and some broken remnants of a fink install, though I'd tried to replace it with brew a while back.Many times I was getting

Library not loaded: /sw/lib/libssl.1.0.0.dylib

However trying to re-install openssl with brew always produced

sudo brew link opensslWarning: openssl is keg-only and must be linked with --forceNote that doing so can interfere with building software.

or

Mac OS X already provides this software and installing another version inparallel can cause all kinds of trouble.

So it was pretty confusing what I should do. What seemed to help in the end, after much trial, included:

$ rm /Users/dan/.rvm/rubies/default/lib/ruby/1.9.1/x86_64-darwin11.4.0/openssl.bundle

which had references to the non-existent /sw/lib/libssl.1.0.0.dylib file.Then

$ sudo brew update && sudo brew upgrade$ rvm reset

brought my version up from 1.9.1 to

$ ruby --versionruby 2.1.2p95 (2014-05-08 revision 45877) [x86_64-darwin13.0]

At which point I had to re-install bundler (?)

$ gem install bundler

But finally I could run 'bundle' on my project and it seemed to behave.