rvm --debug --32 pkg install openssl

gistfile1.txt

__rvm_update_configure_env(6):MACOSX_DEPLOYMENT_TARGET=10.8 CFLAGS= -arch i386 -g -Os -pipe -no-cpp-precomp CCFLAGS= -arch i386 -g -Os -pipe CXXFLAGS= -arch i386 -g -Os -pipe LDFLAGS= -arch i386 -bind_at_load LDSHARED=cc  -arch i386 -dynamiclib -undefined suppress -flat_namespace:
found compiler: gcc-4.2
Fetching openssl-1.0.1c.tar.gz to /Users/aabolts/.rvm/archives
Fetching: http://www.openssl.org/source/openssl-1.0.1c.tar.gz
Fetch command: curl  -f -L --create-dirs -C - -o openssl-1.0.1c.tar.gz
No archive, downloading
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 4352k  100 4352k    0     0  1603k      0  0:00:02  0:00:02 --:--:-- 1644k
Downloaded archive checksum matched.
Extracting openssl to /Users/aabolts/.rvm/src/openssl-1.0.1c
Configuring openssl in /Users/aabolts/.rvm/src/openssl-1.0.1c.
Compiling openssl in /Users/aabolts/.rvm/src/openssl-1.0.1c.
Installing openssl to /Users/aabolts/.rvm/usr

Please note that it's required to reinstall all rubies:

    rvm reinstall all --force

Updating openssl certificates