Just a wild guess but you have installed the ports version of ruby
1.8.7 which is not the default ruby install on osx. Gems are installed
and stored under the ruby install that it was installed with.. Which
means if you installed all the gems in one ruby then added the ports
ruby you need to reinstall your gems...

You script/server might be getting some old path info... ?? I know
when I upgraded to 1.8.7 on the mac I had very similar issues...
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