Fifty Shades of Grayson is the tenth episode of the fifth season of The Vampire Diaries and the ninety-ninth episode of the series overall.


The Vampire Diaries - Fifty Shades of Grayson Trailer

The Vampire Diaries - Fifty Shades of Grayson Trailer


DAMON’S PAST RETURNS TO HAUNT HIMDamon realizes Elena is in danger and enlists Stefan’s help to find her. The brothers pay a visit to Aaron, and Damon shocks Stefan by revealing his first-hand knowledge of Aaron’s family. In an attempt to stop Damon, Dr. Wes unleashes his secret weapon, forcing Damon to deal with a part of his past he thought was gone forever, as well as the consequences of his decades-long plan for revenge. Meanwhile, Elena is horrified by Dr. Wes’ confessions about the dark history of Whitmore College and his own ultimate goal. Finally, a frantic Katherine turns to Matt for help, until she realizes that Nadia may be the one who can solve her problem.



Main Cast

Recurring Cast

Guest Cast



  • Antagonist: Wes Maxfield
  • This episode is the mid-season finale for Season Five. 
  • This is the final episode of the second chapter of Season Five, The Augustine Chapter.
  • Ian Somerhalder described this episode as "beautifully haunting."
  • This episode establishes the series' current timeline as being late 2011, evidenced by Katherine saying that she's 538 years old, and Stefan noting that she had spent 147 years doing bad things to him.
  • Elena's Augustine test subject number is revealed to be 83182. 
  • Enzo is confirmed to be the Augustine Vampire who killed Megan, after Megan accidentally got too close to his cell when she was snooping around Whitmore House at the party in I Know What You Did Last Summer.  
  • Katherine revealed that her father, Mr. Petrov, was a Traveler. This means that Katherine's true species before being turned into a vampire was a witch. Katherine's Traveler heritage also means that Nadia was also a witch before she turned, and, though it is unconfirmed, it is possible that Katherine's later descendants Isobel and Elena could have also been witches before they were turned as well.
    • Katherine also revealed that while she was technically a Traveler before she turned into a vampire in 1492, she never practiced magic in her early life because her father referred to Traveler Magic as "the devil's work," which was meant to scare her and her sister away from the practice. She also claimed that once she turned into a vampire, she never thought about Traveler magic again until this point.
  • Jeremy, Bonnie, Caroline, and Tyler don't appear in this episode.
  • Elena and Damon broke up in this episode, after Damon chose let Elena go so he wouldn't change her into someone like him.
  • Hemodialysis is the correct medical term for the procedure Dr. Wes Maxfield performs on Elena at the beginning of the episode, not blood dialysis, which is what Dr. Maxfield called it.
  • It is revealed that Wes planned to turn Elena into a cannibalistic Ripper as part of Phase 2 of his vampire experiments. He planned to do this with a compound he created that would instantly make any vampire salivate at the smell of vampire blood after being injected with it. Once he had given her the compound, he intended to let her go so she could feed on and kill fellow vampires instead of humans, as he meant for her to be his new Patient Zero after Jesse's death resulted in the loss of his vampire test subject.
    • However, Wes' Patient Zero would later end up being Damon after Wes injected him with the compound in Total Eclipse of the Heart.
    • To explain to Elena how he conditioned Jesse to crave vampire blood, he used the example of Pavlov's Dog. He then went on to tell her that the method he used on Jesse was much too time-consuming, which is why he ultimately developed a compound to create the same effects in a vampire with only one injection.
  • Aaron picked up the syringe with the Ripper compound and took it with him to keep Wes from using it on anyone.
    • Fortunately for Wes, he would ultimately get the syringe back in Total Eclipse of the Heart after Sloan brought him Aaron's bag following his death at Damon's hands. The syringe would later come back into play in that episode, when Wes injected Damon after he and Enzo arrived to attack Wes in retribution for the torture he put them through.
  • Wes admitted to Elena that Grayson Gilbert conducted vampire experiments in the basement of his medical clinic in downtown Mystic Falls. Elena told him that the basement always creeped Elena out as a child, as she was never allowed to go down there.
  • Wes was surprised that Elena (#83182) was still conscious after taking 4.1 pints of her blood, while he compared her to Enzo (#12144) who faded into unconsciousness after having only 2.9 pints removed in 1996. He wondered if it was evolution or luck, but declared the question to be a mystery for another day.
    • The average volume of blood in the human body is 4.7 to 5 liters, with females having less blood volume than males.
  • It was learned that Grayson Gilbert put 3,000 to 4,000 volts of electricity through a vampire test subject (possibly Enzo) on June 25–26, 1999.
  • While talking to Nadia about having a Traveler teach her the spirit possession spell so she could survive in another's body, Katherine appeared to have either a stroke or heart attack and fell down the stairs.
  • It was revealed that Megan King had a picture of herself and Grayson Gilbert because she had a serious heart defect when she was a child, and he saved her life by injecting her with vampire blood. 
  • Elena impulsively burned Grayson's medical journal due to her complicated feelings about her father's work and its implications regarding her own status as a vampire.
  • Katherine attempted to fight to stay alive because she believed Stefan had forgiven her, but he later told her it was going to take more then one night to forgive all the horrible things she has done to him. This conversation appeared to break Katherine's heart.
  • As of this episode, Elena, Stefan, Damon and Matt are the only main characters to appear in every mid-season finale thus far in the series.


  • Grayson Gilbert was last seen in The Departed in a Flashback.
  • Kelly Donovan was mentioned in this episode. She was last seen in Under Control.
  • Nadia and Matt were last seen in Dead Man on Campus.
  • This episode marks the second appearance of Michael Malarkey as Enzo.
  • This is the first mid-season finale to not feature Caroline, Bonnie and Tyler.
    • This is the second mid-season finale to not feature Jeremy.
  • This was the first episode in which we have seen a flashback of Elena as a child.
  • This is the second flashback of Elena that shows her before the events of the Pilot. The first was in The Departed.
  • As of this episode, neither Jenna, Caroline, Tyler, Bonnie, Jeremy nor Matt have had a flashback of their own out of all of the main cast. However, Jenna, Bonnie and Matt all appeared in Elena's flashback in The Departed.
  • Katherine finally accepts that Stefan will never look at her the same way that he looks at Elena.
  • Stefan finally learns about Damon's time as prisoner of Augustine in the 1950's.
  • Stefan and Aaron met Enzo for the first time in this episode.
  • Wes mentioned the Season One finale, when John Gilbert and the Founder's Council burned all of the tomb vampires alive in what used to be Grayson Gilbert's basement of his medical Clinic.


Behind the Scenes

  • This episode had about 2.44 million viewers in USA, which was 0.06 million more than the previous episode.
  • Hashtag during the airing is #SecretLifeofGrayson

Cultural References

  • The title is a pun of the novel Fifty Shades of Grey by E. L. James.
  • The title is the name of the eighth episode in Season Five of Drop Dead Diva.
  • "Patient Zero" or "Index Case" is a medical term for the first carrier of a disease.


Wes: (to Stefan) "Aaron?"
Stefan: "Not exactly. I'm trying to decide how to kill him."
Wes: "Touch him and you'll never see Elena again."
Damon: "Elena!"
Stefan: (to Aaron) "Do not test me."

Katherine: "I don't hear you counting."
Matt: "3, 4, 5, 6, good try."
Katherine: "Good try? That was horrible, Matt. Come on, I'm paying you to make me hot again! Whip me into shape, and I'll prolong this death thing as long as possible."
Matt: (mutters) "Yeah, that'll happen."
Katherine: "What did you say? No, seriously, I didn't hear you. Oh my god, I'm going deaf! I'm going deaf. My entire body is falling apart."

Katherine: "I can't breathe, I can't breathe! Water, give me some water."
Matt: "Deep breaths. Look, if you're so anxious not to be dead, why don't you just have a vampire turn you?"
Katherine: "Tried that. Every time I ingest vampire blood, my body rejects it."

Wes: "Subject 83182 appears conscious."
Elena: "Where am I?"
Wes: "Why? Look familiar?"
Elena: "What is that thing? What are you doing to me?"
Wes: "83182, let's prepare blood dialysis. Count from 10, 9, 8, 7, 6, 5, 4..."

Damon: (to Aaron) "Pop quiz. So, your girlfriend's taken by a mad scientist. Now, do you: A, get a new girlfriend; B, call the police; or C, kill someone close to the mad scientist?"

Wes: "Damon Salvatore is locked in an impenetrable and inescapable fortified cell."
Aaron: "Or he's in front of me imagining what my kidney would taste like."

Aaron: "Why don't you finish the rest of the story, Damon?"
Stefan: "I don't recall saying that you could talk. Did I say that he could talk?"
Damon: "I don't remember anything."
Stefan: "I didn't think so."

Damon: (to Aaron) "I don't like you. I don't like your family. I don't like you messing up my relationship. If you're lying, I'm gonna take my thumbs, and I'm gonna gouge out your sad little eyes out of your sad little head!"

Damon: "And, I'm gonna tell you my side of the story. You asked me if I thought about you after I escaped, and answer is no. And, I sure as hell don't feel guilty about leaving you, because in order for me to save myself and leave you, I had to shut off my humanity, damn it! So, I flipped the switch, and then I felt nothing, no remorse, no regret, no pain."
Enzo: "And now what do you feel, remorse, regret, pain? Even if I forgave you, Damon, would that make you less of a horrible person?"
Damon: "We're even, Enzo."
Enzo: "You were the most important person in my life, and you ruined me. But, that's just who you are. That's who you'll always be... A monster."

Damon: (to Elena) "I won't change who I am. I can't... But I refuse to change you."

Katherine: (pouts) "I'm getting wrinkles."
Stefan: "Heh. Katherine Pierce's chickens come home to roost in the form of wrinkles. It's kind of brilliant."
Katherine: "What's the opposite of funny? Oh, right. Not funny."

Katherine: (to Stefan) "One night... An eternity... You'd never look at me the way you look at Elena, would you?"

Katherine: "I'm a survivor. Staying alive is my specialty."



Last.fm_play.png "Slave" – Yeah Yeah Yeahs
Last.fm_play.png "Fitzpleasure" – Alt J
Last.fm_play.png "Where It Ends, Where It Begins" – Sacco
Last.fm_play.png "The Love Club" – Lorde
Last.fm_play.png "All I Want" – Kodaline




See also

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