of course Dean was absolutely crazy about the one girl he can’t have. it’s his luck right? i mean sure he has his occasional fun, never anything more than a one night stand. he thinks he’s just not fit for relationships but the truth hangs at the back of his mind, it’s unavoidable

Bobby warned him, well more like threatened him

“y/ns off limits boys, try anything & you’ll be picking buckshot outta your chest”

who was Dean to disobey Bobby? i mean sure he thought about you all the time & always made sure to pick out the beer you preferred when he’d go out to the store. hell even skipped out on extra onions on his bacon cheeseburger when he stayed at Bobby’s because he knew how much you hated the smell

Dean was distraught, he knew he wanted you. wanted you so damn bad but he knew he was wishing for the impossible

he’s pulled outta his thoughts as you walk around the pool table & nudge his side, the music rings loudly around the bar

Dean keeps his distance but still has that cocky smirk plastered on his face as he says

“you ain’t the betting type, are you?”