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 openssl
Warning: openssl is keg-only and must be linked with --force
Note that doing so can interfere with building software.

or

Mac OS X already provides this software and installing another version in
parallel 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 --version
ruby 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.

Homebrew changed its version of Openssl to 1.1 days ago (Homebrew/homebrew-core@0349a7c 25 and Homebrew/homebrew-core@b4b9c1c 10). We can downgrade Openssl to the older version to temporarily fix this issue while waiting for the new rebuild to come (or do it manually):

So I solved like this:

brew uninstall --ignore-dependencies openssl
brew install https://raw.githubusercontent.com/Homebrew/homebrew-core/30fd2b68feb458656c2da2b91e577960b11c42f4/Formula/openssl.rb

UPDATE

From catalina you could get a message like:

Error: Calling Installation of openssl from a GitHub commit URL is disabled!

In this case I recomend you to go to the URL and download the content into a file (with name openssl.rb). Then you can do:

brew install openssl.rb