He can be a jerk, he can be short-sighted, and hard-headed. People aren’t perfect, and to have a perfect character doesn’t make sense. I’ve always gravitated toward the flawed characters, the reluctant heroes.
“Well that’s touching considering you don’t have a heart.” - Dean in 11x13 “Love Hurts”
“Oh Tin Man, Tin Man, Where Is Your Heart”, or "In Death Reborn - Why Dean Winchester May Have to Die in Order to Live"
From 1x12 “Faith” onwards the audience has been told that Dean’s heart is special. After almost dying after an electrocution that severely damaged his heart, Sam, desperate to save his brother found a faith healer that laid his hands on Dean and healed him. Unknowing of how that was possible Dean asked Roy Le Grange why he chose to save him out of all the sick people there to which Roy simply replied that he didn’t choose Dean, but “the lord” did. Even after it is revealed that in fact his wife Mary Ann chose who lived and died and with that played God, what Roy told Dean when he asked him “What did you see in my heart?” still rings true as he said he sees “a man with an important purpose that isn’t finished yet”.
Arguably this already related to Dean’s place within the Grand Story, this first focus on Dean’s heart, especially since the show is giving this very organ connoted to be the center of a person and the place of emotions and with that love (something Dean as a character has always been about) at the moment as much attention as almost never before while with the arrival of the Darkness we witness the rewrite of the Grand Story, the state of Dean’s heart is re-examined too.
This week’s episode, 11x13 “Love Hurts” was a milestone in that regard as it dealt with the heart front and center and has been emphasizing a couple of things that have been foreshadowed heavily all throughout the season: that Dean Winchester is incomplete and will have to die (in order to live).