How You Met--
Dean: You met him at bar after he had finished a hunt with his brother. He looked tired, and maybe needed someone to talk to. So you leant an ear, and gave some warm words of comfort You wrote your phone number on a napkin, and told him you would be happy to see him again some day, and he was very welcome to call if he needed someone to talk to.
Sam: You were sitting at the library reading up on your little towns local history. While you were reading, a very tall man sat across from you and asked if he could take a quick look at a page from the specific book you were currently reading.
Cas: You were on a vacation with your friends Sam and Dean. A little get away cabin in the back woods of Tennessee that you owned as a safe house, and vacation spot.
You and the boys were swimming in the little pond on the property, when fwoosh! A man in tan trench coat appeared at the waters edge. You were about to ask him why he was trespassing on your property, but Dean spoke up. ...