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From a young age dean had been forced into a life that he's not sure fits him quite right. At the age of four he was a protector of his younger brother, Sam, this is something that continues to follow him through life and some may even say is the reason Dean exists. After that, until dean was well into his early 20s he was the perfect soldier that John Winchester wanted him to be. He never stepped out of line, he took care of Sammy, he learned to fight, learned to shoot a gun instead of how to throw a baseball, he even seemingly pushed aside his own internal debates about sexuality and gender to fit the mold that John had so carefully curated for young dean.
The life that Dean lived was not selfish, he was potentially one of the most selfless people to walk the earth. Afterall, there is a reason why heaven calls him the righteous man. To be righteous is to be virtuous, synonymous with the concept of being worthy. Worthy of love and adoration, of respect and held with the highest esteem. This is how the world, how heaven, sees Dean. however this is not how Dean sees himself.
Every day Dean lived his life with a pessimistic outlook; that one day, potentially even soon, he would die and that death would be violent and painful. Nothing graceful nor worthy of a righteous man. But rather ugly, violent and monstrous. Dean's death would be nothing more than an event bound to happen, nothing to mourn nor grieve for he believed his soul had been lost long before his inevitable death. Though this isn’t to say that Dean would have taken his own life in moments of desperation, no Dean would never hurt Sam that way. Hell he wouldn't want to do that John. Instead Dean had hoped his life would be short, he would accomplish all that he was set out to do and save as many lives as he could but eventually he would not get to grow old. He had never believed that he would be able to see the fruits of his labor. That was the path laid out in stone for hunters.
Dean's life of hunting was thrust upon him, an existence forged by his ancestors and continued by John's continual need for revenge. At a certain point it is truly a wonder how dean managed to live his life for as long as he did, but the earth needs righteous men; the earth needs dean winchester. Hunting monsters and saving people was all that Dean had seen for his existence, however short or long it may be. His aspirations of living a life outside of hunting were fictitious at best, something he may have dreamt of before the age of 17.
The loss of innocence felt on Dean's 17th birthday is perhaps more critical in the development of Dean's self image and worth than any other event. A day intended to be full of love and celebration of life and accomplishment up to that point, instead shrouded in pain and fear. The day John decided it was time for Dean to go out on his first ever solo hunt. A test of will, a way to see if dean had the stomach to kill two innocent and misguided ghosts who were not too unlike himself. John's assignment under the guise of a rite of passage and a way to spend time with Sam. It was Dean's birthday afterall, no better time than the present.
A haunting in RIverton, Wyoming at St. Stephens Indian Mission, something that John even helped to scope out to test the level of haunting and how the ghosts were tied to the mission. However, this is where John's intentions take on a more menacing reality. The ghost haunting the mission were two nuns, they were in love with each other but this love was a multilayered sin; they had loved each other in the way God intended a man and woman to love to each other and as two women this was unacceptable in the eyes of God and especially in the eyes of John Winchester. Though that was not their only sin, their love was sin enough but the true salt in the wound was that they had found peace and comfort in one another. The love and adoration held for the other was borderline worship and religious in its own right, a sin of treachery worthy of the ninth circle of hell where they would reside frozen for all eternity as punishment for loving each other more than they loved God. Once the Nuns were discovered it is unclear whether they killed themselves as an act of preservation or if the men around them persecuted the women for their love. Either way their death was violent and unwarranted leaving their souls behind to forever haunt St. Stephens Mission, left behind to become corrupted and skewed versions of themselves. These were the ghosts intended for the 17 year old dean to hunt and kill for a final time.
The very same dean who is said to have been found with another boy his age in a compromising position, but that's neither here nor there.
At the end of the day dean accomplished his mission, but not without losing a certain glint in his eyes. His return was met with a happy, if only slightly grumpy, 13 year old Sam who had just spent the whole day with his father. John's reaction to Dean's return was hopeful, thinking that perhaps he has dissuaded Dean's diversions enough for the time being.
What John didn't realize was that the damage he had caused would be felt by Dean for the rest of his life, raising questions of worth for both life and love. Cracks so large that an angel from heaven could not repair them when he put Dean back together atom by atom. Cracks that would not heal until Dean unlearned his fathers lesson and learned how to love himself and life, and maybe even the aforementioned angel.