First ,installing ruby19 is easy,add some options in portage configure files.
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RUBY_TARGETS="ruby19"
in /etc/make.conf
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echo "dev-lang/ruby" >>/etc/portage/package.keywords
,cause ruby19 is masked in Gentoo(from this,the ruby are not supported as good as python:)
Then the rubygems,it's really hard,from mine,rubygems 1.3.7 just support ruby18,jruby.and i found out that the rubygem 1.3.7-r4 support ruby19,so just do like this:
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emerge "=rubygems-1.3.7-r4"