[Writing prompt for the word 'Harry Potter'. Also based off of a current AU rp.]
Dean was always more of a Rocky Balboa and a Batman kinda guy so when Jessica shows up at his door with the entire set of Harry Potter, he frowns and slams the door. Of course it didn't stop her from just barging in and slapping the back of his head and telling him to get the DVD player ready because he was stuck watching it whether he wanted to or not.
After about an hour of trying to whine and fake sob his way out of it, even trying to pull the whole 'but I have whipped cream in my ass' bit on her, they finally came to the agreement that they would watch the movies and Jess owed him babysitting for the next million years.
The first movie was lame. It was all fake and it was obvious that the moral of the story was to not go with giant biker guys or they'll give you drugs and make you think you can walk through walls and fly on brooms, which he was totally trying later. The second movie was better because well, there was a chick who lived in a toilet and Dean thought that was hilarious.
The movies got better and he started yelling at the screen like he was watching football and by the time they got to the seventh movie, Dean actually liked this shit. He even felt a few tears when Dobby died, which he would never admit. But Jessica was loving every second of it, curling into Dean's side and laughing when he got too riled up, even punching his arm when she got over excited and screamed at a few parts. It was the actually worth watching.
So by the end of the eighth movie, Dean apologized and told Jess she only owed him for half a million years of baby sitting. She just laughed and told him to shove it, laying against him and falling asleep, Dean soon to follow.
Yeah, it was worth it.