Dean W

(this is as good as the detail would get in the photo, but sorry about the face) You and him knew each other for 8 years now. He was being his usual self, flirting with the waitress. You were going out with your friends, but it looked like you guys were either going to a strip club and or somewhere fancy, you guys walked into the dinner more skin showed then ever before. It was the first time he saw you with a revealing outfit -any outfit of your choice- (I hope this is isn't too bad, but continue the story from there and yes everybody in supernatural is in this if you want, or it could just be you and him)