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5 Times Dean Winchester Broke the Supernatural Fandom’s Heart

5 Times Dean Winchester Broke the Supernatural Fandom’s Heart

Supernatural spoilers ahead! If you aren’t caught up, read on at your own risk!

Supernatural is notorious for breaking its fandom’s heart, from killing favorite characters to just general soul-crushing feelz. While Jared Padalecki’s Sam Winchester has his own share of heartbreaking moments on Supernatural, Jensen Ackles’ Dean Winchester has also done quite a lot of breaking the fandom’s heart in the past decade. Of course, because Dean feels things so deeply and feels guilty for nearly every bad thing that has happened in the world (I mean, Sam gets the press for starting the apocalypse, but the whole thing started thanks to a righteous man…) it doesn’t take a lot to get us a heartbreaking Dean moment.

We’ve certainly got a lot to choose from, so I decided to focus on heart breaking moments including Dean’s ultimate weak spot: his family (though there are also LOTS of moments to choose from there). Here are five of those family-related, fangirl soul-crushing moments.

Dean’s Heaven

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It’s no secret that Dean cares about his little brother Sam more than just about anything in the world. Dean sold his soul to bring his brother back to life, and after getting a glimpse of his personal heaven, we saw how important Sam truly is to Dean. After Sam and Dean are shot dead and sent to heaven, Dean wakes up in his Impala, reliving a nice memory of him and Sam shooting off fireworks when they were kids. It’s really quite sweet that Dean’s idea of eternal rest is simply having a fun time with his brother.

Why is this moment particularly heartbreaking? Mainly because, while all of Dean’s heaven-memories are focused on his family, all of Sam’s best memories surround times where he was away from the family–spending Thanksgiving with another family, running away from home, and going away to Stanford–which seriously hurts Dean.

Dean Dealing With Charlie’s Death

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I’m still upset about Charlie’s death, you guys, but it’s no secret that her death really took a toll on Dean. If there is anything Dean takes seriously, it’s protecting his family, and he considered Charlie to be a little sister to him. The fact that one of the last moments they spent together before her death involved him hurting her thanks to The Mark causing him to lose control, and then knowing she died trying to find a way to cure him of The Mark made her death an even harder reality to accept for Dean. But hey, I’ve got a great way for Dean to get over Charlie’s death.

Bring back Charlie. See? Easy!

Erasing Himself from Lisa and Ben’s Memory

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Outside of his biological family and hunter family, Dean’s really only had one real shot at having a family of his own, and that was with Lisa and her son Ben. While Ben might not be biologically Dean’s, Dean loved Ben and Lisa a ton, even having dreams of living a normal life with them. I know some of the fandom didn’t like Dean with Lisa, but I loved them as a little family. It wasn’t perfect, but for once Dean was happy (mostly–Sam was in the pit, so Dean wasn’t 100% but still).

Of course, it didn’t take Dean long to realize that his mere existence near Lisa and Ben would put them in huge amounts of danger, and he has Castiel erase all memories of him from Lisa and Ben’s memory. Dean is fantastic with kids, and he’s such a protector and a natural paternal figure. The fact that leaving Lisa and Ben means he likely lost his chance to be a dad and have a family–and will probably not pursue having his own family again–is just tragic.

The Djinn Dream

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After being taken by a djinn, Dean is thrown into a dream where his life is the nice “apple pie” life the Winchesters never had. Sure, he and his brother don’t have a great relationship, and his life isn’t perfect; but his mom is alive, their dad died of a heart attack (not a demon attack), Sam is engaged to Jessie, and Dean is in a relationship with a girl who is madly in love with him. Dean sees his family healthy and safe, and it makes Dean blissfully happy. I mean, if it doesn’t warm your heart to watch him happily mow is mom’s lawn, I submit that you have no heart.

The longer he stays in this world, the more holes he starts to see in it. Ultimately, he realizes that the world around him isn’t real at all, but is a projection from the djinn holding him captive, and he’s faced with a choice: stay in the dream and die happy with the family and life he’s always wanted, or destroy the dream and go back to reality where his parents have both died horrible deaths and he and his brother are constantly in life-threatening danger. Despite how happy he is in the djinn dream, Dean ultimately chooses to return to reality, forcing him to say goodbye to his mother again.

Dean’s Speech to Dead Sam

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This one is truly brutal. It’s no secret that Sam and Dean die a lot, but we weren’t as used to the whole “Winchesters never die” thing in season 2 when Sam was stabbed by one of the other people “chosen” by Azaezel. Dean brings Sam back to Bobby’s, and in a fit of sorrow ends up monologuing at Sam’s corpse for a bit. Having just lost his dad under unimaginable circumstances and then losing Sam only to find him moments before his death is too much for Dean. He’s alone, he’s lost, and he feels like he’s failed at his most important job–protecting Sam.

Listening to Dean beat himself up and sit in complete heartbreak and despair is brutal, and there’s no way to watch that speech without getting a bit misty. Things only get worse when Dean decides that the only way to make things right is to trade his soul for Sam’s life. Watching Dean completely hopeless, beating himself up, and then literally damning himself is brutal to watch.

What do you think are some of the most heartbreaking Dean moments on Supernatural? Let me know in the comments!

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