Supernatural 10 Times Dean Winchester Broke Our Hearts

Supernatural: 10 Times Dean Winchester Broke Our Hearts

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As part of Supernatural’s pair of sibling heroes, Dean Winchester has been through hell (literally) on the show. The hunter has brought fans to tears.

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Supernatural 10 Times Dean Winchester Broke Our Hearts

With only one season left of Supernatural, fans are reminiscing about the “road so far,” remembering all of the feels Sam and Dean Winchester have delivered over the past 14 years. It’s almost overwhelming to think about.

Despite Dean presenting such a hard shell to the outside world, his vulnerability has been exposed every single season, sometimes so raw and poignantly it moves us to tears. Whether he’s meant to or not, and whether it was out of his own terrible deeds or the sorrows he’s experienced, Dean Winchester has broken our hearts several times over the years. We’re still recovering from some of these moments.

10 He Offed Sam’s Friend

Supernatural 10 Times Dean Winchester Broke Our Hearts

Her son vowed revenge, but it’s been years since he did and the show only has one season left to go. Fans are speculating that by now, the boy, Jacob Pond, has grown, gotten strong and is ready to fight a Winchester brother in honor of his mother’s passing. We don’t doubt that Dean would do the same.

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9 He Cried At John’s Grave

Supernatural 10 Times Dean Winchester Broke Our Hearts

Dean demanded, “Why is it my job to save these people? Why do I have to be some kind of hero? What about us? Why do we have to sacrifice everything, Dad?” As tears pour down his face and we realize he’s saying what he could never ask while his father was alive, we weep with him.

8 When He Was Offed Over And Over Again

Supernatural 10 Times Dean Winchester Broke Our Hearts

It was ridiculously too much to handle and we got lucky that some of the moments were so funny because it was so difficult to see Dean offed again and again.

7 When Metatron Offed Him

Supernatural 10 Times Dean Winchester Broke Our Hearts

Dean had a hard time dealing with the Mark of Cain the entire season and we knew something bad was going to come of it, but he went ahead and broke our hearts double-time as he left Sam to go party hard with Crowley, leaving poor Sammy to search for his big brother. Seeing Dean completely careless about Sammy was just too much.

6 When The Hellhounds Got Him

Supernatural 10 Times Dean Winchester Broke Our Hearts

To add insult to serious injury, we learn that not only was Dean in Hell for forty years instead of four months, but he also became one of the minions who tortured other souls while trapped in Hell. Had we known what else was in store for Dean down the road, perhaps it wouldn’t have broken our hearts so hard.

5 He Left Lisa And Ben

Supernatural 10 Times Dean Winchester Broke Our Hearts

It wasn’t just the loss of Squirrel’s happiness that got us in the gut, but how he had to leave his newfound family. Dean had to erase Lisa and Ben’s memories of him to keep them safe, eliminating many of the best moments of his life from their minds. It was one of his most heartbreaking sacrifices and remains so to this day.

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4 He Left Adam In The Pit

Supernatural 10 Times Dean Winchester Broke Our Hearts

Jensen Ackles and Jared Padalecki have joked about this on comic con panels, but in reality, fans believe it’s something that will have to be addressed this final season. After all of that time spent in the pit, Adam likely isn’t going to be very friendly toward his estranged brothers, either.

3 When Castiel Almost Killed Him

Supernatural 10 Times Dean Winchester Broke Our Hearts

It proved Dean’s devotion to the angel, and it became a key point in their timeline Dean/Cas shippers, or “Destiel” shippers, particularly when Dean pleaded, “Please,” to his friend. Affirmation of this ‘ship is another final season plot point many fans hope to see.

2 When He Went To Heaven

Supernatural 10 Times Dean Winchester Broke Our Hearts

When he and Sammy were shot and sent to Heaven, it was even more affecting because we witnessed what Heaven was to him: Childhood moments spent with Sammy. It still chokes us up to think about it, especially since Sam’s Heaven was made up of moments away from his family, which is even more heartbreaking.

1 He Kept Castiel’s Coat

When Dean folded it up like a soldier’s flag, there wasn’t a dry eye in the audience. Ackles and Padalecki have both poked fun of the episode, which has been compared to the equally moving one at the end of the film Brokeback Mountain, but it remains one of the most heartbreaking moments in the history of the show.

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