Best Chick Flick Moments On ‘Supernatural’

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From Season 1, Dean Winchester made a solid request, “no chick-flick moments.” Unfortunately for the demon hunter, the past 13 seasons have been chock-full of them. In a world where monsters are real and the dead are given a second, third, and a fourth chance at life, Sam and Dean have seen their fair share of terror. They’ve faced Ghouls, Ghosts, Zombies, Leviathans, Angels, and even God’s vengeful sister, and yet the scariest thing Dean has ever faced are the chick flick moments the Winchesters have gone through since 2005.

As much as we love Dean, we’re adding to his torture with some of the best chick flick moments we’ve ever seen on Supernatural.

Season 1 Episode 1: “Pilot” – Sam and Dean are on the hunt for their missing father, but while on the case, they are sent to a sleepy town to track down The Woman in White. Tensions run high and an altercation with the spirit leaves Sam and Dean at one another’s throats. Unresolved issues between the boys have sparked some hostilities. After having time to cool off, Sam begins to apologize to his brother, but before he can finish, Dean raises his hand in the air and says, “No chick flick moments.”

Season 1 Episode 9: “Home” – If the title of the episode doesn’t send shivers down your spine like any good emotional chick flick, the scene where Dean calls his father in secret will. When a case leads the boys back to their childhood, the very one where their mother burned and died on the ceiling of Sam’s nursery, Dean makes a gut-wrenching phone call to his father. Visibly shaken and on the verge of tears, it is the first time we truly see just how tormented the older Winchester brother really is.

Season 2 Episode 17: “Heart” – After losing his long-term girlfriend, Jessica, in the same manner that the boys lost their mother, Sam was unable to open up to people again, mainly women. That is until he met Madison, a woman being stalked by a werewolf. The two begin to bond and ultimately sleep together and it seems as though Sam is beginning to have faith in happiness again. Don’t get too excited; this is Supernatural after all. As it turns out Madison has been bitten by that same werewolf and upon the rising of the full moon makes her transformation. The following morning, Madison, desperately not wanting to risk hurting or killing anyone, makes a gut-wrenching request of Sam. She pleads with him to kill her so she is no longer a risk. With tears streaming down his face and Queensryche’s “Silent Lucidity” adding to the sadness, the screen cuts to black as a gunshot rings out.

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Season 2 Episode 22: “All Hell Breaks Loose” – In a shocking twist, Sam Winchester is killed in the first part of the two-part season finale at the end of the second season of the hit CW series. It is a death that Dean Winchester does not have the strength to handle. In probably one of the most chick-flicky, gut-wrenching moments of the series, Dean sits beside Sam’s lifeless body and begs for an answer as to how to move on.

Season 3 Episode 7: “Fresh Blood” – Dean, knowing his trip to Hell was coming soon, decides to take his little brother under his wing and teach him everything he knows about cars. Well, one car, his 1967 Chevy Impala most lovingly known as “Baby.” Fans love seeing the brothers bonding and doing “normal,” brotherly things; however, if Dean knew he was coming back from Hell a few months later, he probably would not want to watch this scene.

Season 4 Episode 16: “On The Head of a Pin” – After doing some not-so-chick-flicky-things to the demon, Alistair, Dean finds himself on the wrong side of the angry demon, which ultimately lands him in the hospital. The boys have been trying to prevent the demon, Lilith from breaking the 66 Seals and releasing Lucifer from Hell; however, Castiel is about to drop a bomb on his best buddy. During his time in the pit, Dean tortured souls, thus breaking the first seal. Realizing he is the reason that the door to Lucifer’s cage began to open, Dean begs his angel friend, Cass, to find someone else to stop Lilith as he no longer has faith in himself.

Season 7 Episode 17: “The Born-Again Identity” – Castiel and Dean’s friendship started out rocky, what with Castiel insisting that Dean show him some respect or he would throw him back in the pit from which he came. Still, their bond grew over time and when Castiel switched places with Sam in the looney bin and literally lost his mind for the brothers, Dean held out hope that his pal would one day return to normal. Throughout the season Dean has been holding onto Cass’ recognizable trench coat in the hope that one day he could return it to his angelic friend.

Season 8 Episode 23: “Sacrifice” – Throughout the course of the season, Sam has been completing various trials in order to close the gates of Hell forever, but the trials have taken a toll on his body. With only one trial left, Dean stops his brother, telling him he’s done enough and it’s not worth ending his life over. The trials stop and the gates of Hell remain open, but Dean still has his brother.

A running theme of the show becomes about the sacrifices the boys make for one another. Demon deals or switching places to sacrifice their lives for one another, nearly every episode has at least one moment that Dean would consider a chick-flick moment. Guess his rule about not having any of them went poof — just like every spirit they’ve ever vanquished.