This really happened on the show huh
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Dean Winchester every day -- 25/326
Supernatural 2x03//Bloodlust
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Okay so we know that Dean was at Sonny’s for two months in the Spring of 1995—it was either March-April or April-May, because the wrestling trophy was April 1995. I think it’s safe to assume the latter, because we know that, while Dean was at Sonny’s, Sam was with Bobby & John was hunting, and that William Harvelle died on May 16th 1995 while on a hunt with John. It seems likely that it was after this hunt that John picked up Sam and then went to get Dean, too, which leads us to the third thing that happened in 1995 (or, I suppose, sometime before January 23, 1996): the hunt Dean told Gordon about from when he was 16.
That scene (In 2x03 (Bloodlust)) is SO interesting to me because even outside of the context of later seasons, the wording and acting are both super interesting: Dean is clearly telling a story and playing it up a bit, but the words themselves aren’t overtly positive; instead, they emphasize that Dean is set apart from normal kids—“seeing things they’ll never even know. Never even dream of.” Gordon is smiling as he listens, grinning as he states that Dean “embraced the life” but Dean’s face is serious & contemplative as he agrees. The acting on both sides makes it abundantly clear that the two have different understandings of “embracing” the life: when Gordon says it, there’s an aspect of enjoyment that isn’t there when Dean is talking about it.
In context, though, and particularly in context of 9x07 (Bad Boys), Dean’s story is even more compelling: by Dean’s own account, he was 16 when this hunt happened, so either he went on this hunt between January and April (or possibly March, depending on when he was at Sonny’s)—before Sonny’s—or, more likely, sometime after he left Sonny’s. If we assume it was after—at most eight months after Dean tasted normalcy and John lost Bill Harvelle—Dean’s words gain another layer, especially the line “I’m sixteen years old. Kids my age are worried about pimples, prom dates…” because, as we know, Dean spent part of his time at Sonny’s getting to know & flirting with Robin, and was going to go to the dance the same night he ended up leaving, only deciding to go when he saw Sam in the Impala with John & knew he couldn’t leave him alone. In light of that, it’s clear that this line is not Dean looking down on the normal life, it’s Dean giving up on something he once wanted, coming to terms with his life as best he can.
In summary: John left Sam and Dean alone, and Dean got caught stealing food for them to eat. Dean went to a home and Sam went to Bobby’s and John went on a hunt and lost a friend. John picked up his boys and kept hunting, bringing Dean with him (putting him in danger, as he well knew considering what had just happened with Bill) while leaving Sam in the car (neglecting him). Dean stood in front of a fire as a body burned and watched as the dreams he’d let himself have for a short time burnt up with it, and even years later, recalling the scene fondly, couldn’t quite manage to sound like he was happy about the idea of letting them go to embrace the life.
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