ruby-build failed me, so I took matters into my own hands. Here's what worked
download and extract ruby 2.0.0p-195 to ~/.rbenv/src/ruby-2.0.0p195
mkdir $HOME/.rbenv/src
cd $HOME/.rbenv/src
wget ftp://ftp.ruby-lang.org/pub/ruby/2.0/ruby-2.0.0-p195.tar.gz
tar xzf ruby-2.0.0-p195.tar.gz
Install openssl-0.9.8 with homebrew (assumes homebrew is installed to /usr/local)
cd /usr/local/Library
git checkout a2e8b543f16745025001790777770b190b5d9a64
brew install openssl
git checkout master # switch it back
Build ruby. (openssl will fail)
cd ~/.rbenv/src/ruby-2.0.0-p195
./configure --prefix=$HOME/.rbenv/versions/2.0.0-p195
make -j 8 # cores * (hyperthreading ? 2 : 1)
make install
set to use ruby interpreter. At this point, ruby 2.0 works but openssl library will not load.
rbenv local 2.0.0-p195
Build openssl against openssl-0.9.8:
cd ext/openssl
ruby extconf.rb --with-openssl-dir='/usr/local/Cellar/openssl/0.9.8/'
make
make install
You should have fully functioning ruby 2.0 with openssl!
@timcharper Have you made any progress? No solutions are working for me with Ruby 2.0.0-p247 and openssl 1.0.1e.