Minnesota Monday: How It Hurts by Ruby Isle By David Erickson | April 19, 2010 | 0 Music video for How It Hurts by Ruby Isle. Found at YouTube from rubyisle. Amazon: Ruby Isle MP3s| How It Hurts MP3 Posted in Videos and tagged 2000s, 2008, Aaron LeMay, Dan Geller, Mark Mallman, Minnesota, Ruby Isle, United States