I tried to install cocoapods (http://cocoapods.org/) on my OSX Mountain Lion.
moshe-mbp:~ moshem$ gem install cocoapods
ERROR: Could not find a valid gem
You can try to update OpenSSL from source instead:
curl -L -O http://www.openssl.org/source/openssl-1.0.1b.tar.gz.asc
curl -L -O http://www.openssl.org/source/openssl-1.0.1b.tar.gz
gpg --verify openssl-1.0.1b.tar.gz.asc
tar xvzf openssl-1.0.1b.tar.gz
cd openssl-1.0.1b
perl ./Configure shared zlib --prefix=/opt/local darwin64-x86_64-cc
make
make test
sudo make install
source