I went out this past summer to the Venice Boardwalk and tried my own free hugs... Yeah.. I'm somewhere between charming and social anxiety..so that was a scary experience. I hugged 3-4 homeless dudes and a cute hippy girl. I then put down my sign and chatted politics with a booth. I would say if you want to get over your shyness through free hugs, just keep calibrating yourself to it. Go out and hug 1 person. Then hug 2. Baby step it until it doesn't bother you. As well..hanging out with a bunch of free-hug folk will make it seem less odd. If you want to make that seem easy..try doing it by yourself.