I had trouble running bundler on this blog because of a ruby error. Though I am not sure what I have broken for this to occur, it appears that ruby could not find openssl libraries anymore. A quick search on stack overflow pointed me on the right direction. Apparently upgrading openssl via homebrew breaks ruby dependencies. What I had to do was to install another ruby version with my ruby manager of choice (rbenv):
CFLAGS='-g -O2' RUBY_CONFIGURE_OPTS=--with-openssl-dir=`brew --prefix openssl` rbenv install 2.2.0 rbenv global 2.2.02 rbenv rehash gem install bundler
And that was enough to bring me back to square one.