OS Xでruby-installでRubyを入れる ref: http://qiita.com/KitaitiMakoto/items/677868276a8f7d5a5ce8

file0.txt

% ruby-install ruby-2.3.3

file1.txt

(snip)
Undefined symbols for architecture x86_64:
  "_rb_ary_resize", referenced from:
      _ary_resize in resize.o
  "_rb_cArray", referenced from:
      _Init_resize in resize.o
  "_rb_define_method", referenced from:
      _Init_resize in resize.o
  "_rb_num2long", referenced from:
      _ary_resize in resize.o
ld: symbol(s) not found for architecture x86_64
clang: error: linker command failed with exit code 1 (use -v to see invocation)
make[2]: *** [../../../../.ext/x86_64-darwin15/-test-/array/resize.bundle] Error 1
make[1]: *** [ext/-test-/array/resize/all] Error 2
make: *** [build-ext] Error 2
!!! Compiling ruby 2.3.3 failed!

file2.txt

% brew upgrade openssl

file3.txt

% brew info openssl
(snip)
For compilers to find this software you may need to set:
    LDFLAGS:  -L/usr/local/opt/openssl/lib
    CPPFLAGS: -I/usr/local/opt/openssl/include
(snip)

file4.txt

% cd ~/src/ruby-2.3.3

file5.txt

% make clean
% LDFLAGS="-L/usr/local/opt/openssl/lib" CPPFLAGS="-I/usr/local/opt/openssl/include" ./configure --prefix=$HOME/.rubies/ruby-2.3.3
% make
% make install

file6.txt

% chruby
   ruby-2.2.3
   ruby-2.2.6
   ruby-2.3.3