Dark Charlie tries to attract him to the darker side of things, tricking him into letting her kill Russell Wellington, the man who killed her parents and suggesting that Dean let her do it on purpose. Once again they bid good byes but not before Charlie tells him from all she has read, she knows they will pull through, encouraging Dean to carry on, they then share a Star Wars-esque moment before she departs.

You're not gonna hurt me, in fact that's your problem. Though Sam and Dean both tell her to give him what he wants, Charlie decides she can't do that, even at the cost of her own life as it means betraying Sam and Dean and giving the Stynes a source of unspeakable evil. Charlie was initially terrified, having read Frank's encrypted hard drive, revealing what was going.

Oh Sam, you're adorable.

In all that time, Supernatural has had a multitude of actors come and go, playing roles big and small.

Charlie insists on helping Dean solve the Mark of Cain problem and promises that they will find a way and he will succeed as he's a Winchester. After their previous encounter, Charlie got into LARPing and was the "queen" of an army.

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Directing her to the base, Sam and Dean learn from Charlie that she'd taken an interest in hunting, and followed all their exploits in the Carver Edlund books, before stumbling on a case of a man with liquefied internal organs. When Charlie was about to be decapitated, Dean and Arthur stormed the camp and rescued Charlie who was confused by his identity but accepted the rescue. After figuring out how to translate the Book of the Damned, Eldon Styne arrives, demanding the Book though she only has her notes on it. With Sam in no condition to hunt, Charlie volunteers to accompany Dean on the case, proving her competence on the firing range and dragging Dean through an honest-to-Chuck montage of outfit-shopping for her new FBI role. The witch however attacked and threw Dean, she tried to kill him, but Charlie dived forward taking the blast, killing her. You're not gonna hurt me, in fact that's your problem. Take your favorite fandoms with you and never miss a beat. Dean was also slightly worried when Charlie left with Dorothy for Oz, but nevertheless let her go, knowing she wanted to go her own adventure. Charlie is one of two people Dean considers as a sibling, the other being.

Dean was noticeably proud of Charlie for killing the witch, however, when Charlie confronted him on bringing her back from the dead, Dean assured her that she would be fine and was still her, but she couldn't tell Sam. Dean and Charlie first met when they confronted her in her apartment. Ezekiel warned it would mean he would have to spend even more time in Sam, more than either of them wanted and would render him unable to help them with the witch. During the confrontation, Dean tried to convince Charlie to go wait in the Men of Letters dungeon which was the safest place, but Charlie refused. It was really lovely. Along with Gerry, Charlie and the brothers hunt the woods for the creature. Mysterious murders by an invisible creature brought the brothers face to face with Charlie again.

In his anger, Dean kills at least twenty people before going to confront Eldon. When he discovered it was a setup and she was captured by angels, he decided to rescue her and was … He then demands that Sam stop the translation of the Book of the Damned which he does until he gets Charlie's email and sees it as his chance to cure Dean. Sam and Dean spot Charlie on the ground. As the rift was closing, Dean wanted Charlie to come with him to get her away from the chaos but she told him she had to defend her world and told him to find a way to stop Michael.