According to install curb gem on Ruby you might be getting hit with 32 bit/64 bit compatibility problems. Maybe you need 64 bit openssl? will probably need zlib too. Try reinstalling:
- $ brew uninstall openssl
- $ brew install --64-bit openssl
and i'm guessing here, but maybe
- $ gem install curb -- --with-ldflags='-L/usr/local/Cellar/openssl/0.9.8s' (or whatever your corresponding version is)