Playing games with the brothers. Y/n has knows the Winchester brothers since forever. Y/n and Dean were old friends, they hunted together and just goofed around together. Y/n’s the same age as Sam, the younger brother who’s been developing a secret crush on Y/n, but his brother being so flirty and such a womanizer, he didn’t dare to act on it. Now they’re in a crappy motel room, Y/n sandwitched between them on the couch as they try to decide what to do in their boredom. Eventually Dean comes up with the idea of playing spin the bottle.