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You need to make it so openstudio.rb is in your Ruby search path. There are several ways to do this. You can set the RUBYLIB environment variable to include the path you the openstudio.rb you want to include. I personally write a file named openstudio.rb to my Ruby installation's lib\ruby\site_ruby directory which loads the openstudio.rb I want from an absolute path. For example, I have the file C:\Ruby27-x64\lib\ruby\site_ruby\openstudio.rb which has as content:

require 'C:\openstudioapplication-1.5.0\Ruby\openstudio.rb'