there should have been an episode where dean and cas both go on really bad blind dates like everything goes wrong and they both want to make it work but it is just disaster after disaster cas spills all his drinks on his date dean accidentally gets into a hunt halfway through and commits murder in front of his date and so at the end of the episode they just meet up at a diner, cas covered in spilled drinks and dean covered in blood and they share dessert and are like man dating is hard while arguing about the bill