Sitting in a dirty chair alongside their hotel’s empty pool, Dean mourned the loss of his normal life. He didn’t work in a garage, and he didn’t date a nurse. Sam and Jess were not engaged and living in California, and his mother was not alive.
In Dean’s perfect world, people constantly asked him if he’d been drinking. He and Sam never spoke outside of holidays, and Dean was a disappointment to his family.
In the not-so-perfect world, Dean was a hunter, just like his father had been. His Sam didn’t wear preppy clothes, and knew the appropriate response to being called “Bitch.” His Sam remembered that Dean still called him Sammy on occasion. Neither of them had ever mowed a lawn before, and they probably never would.
For one brief moment, he had been free. He’d been free from the never-ending hunt, free to sleep at night without nightmares plaguing his sleep. But Dean Winchester was not normal, and neither was his brother. There was a demon after them, and countless other demons who needed to be killed. They saved people’s lives, and sacrificed their own. According to Sam, it was worth it. Dean wasn’t so sure anymore.