I think I figured out the problem. The library (fsevents) was calling "osx/foundation" and the machine that had the problem didn't have RubyCocoa installed. After I installed RubyCocoa it worked perfectly. It's just strange that it said that it couldn't find fsevents.rb when the problem was actually with osx/foundation.
And to answer your questions, the value of $: for me is: "=> ["/opt/local/lib/ruby/site_ruby/1.8", "/opt/local/lib/ruby/site_ruby/1.8/i686-darwin9", "/opt/local/lib/ruby/site_ruby", "/opt/local/lib/ruby/vendor_ruby/1.8", "/opt/local/lib/ruby/vendor_ruby/1.8/i686-darwin9", "/opt/local/lib/ruby/vendor_ruby", "/opt/local/lib/ruby/1.8", "/opt/local/lib/ruby/1.8/i686-darwin9", "."]"