DAMON’S PAST RETURNS TO HAUNT HIM — Damon 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.
Damon escapes from his cell and goes straight back to the Salvatore house looking for Elena. Instead, he runs into Katherine who had just run away from Stefan's bedroom because she found more grey hair and she panicked. Damon asks her if she saw Elena and Katherine is sure to inform him about what happened between her and Stefan the previous night.
Damon tells Stefan that he can't find Elena and they both head to the university to find Aaron since he is the only one who can help them track her down. Aaron is surprised seeing Damon alive since he shot him on the head and he tries to run away with no luck. The two brothers use him as leverage to get Elena back. Aaron calls Wes and tells him that Damon and Stefan will kill him if he won't give them Elena. Wes agrees for the exchange and tells Aaron to meet him at his classroom.
Wes doesn't keep his word and instead of going to his classroom with Elena, he releases Enzo and sends him there to solve his unsolved business with Damon. Before he sends him, he injects him with poison telling him to not come back for the antidote unless he kills Damon. Damon, Aaron and Stefan arrive at Wes' classroom but they find only Enzo. Stefan calls Wes but Wes is not willing to come and threatens Stefan that he will kill Elena if they hurt Aaron only to get the answer from Stefan that the threat goes both ways. Damon volunteers to kill Aaron when Stefan informs him about the phone call and Aaron, to save his life, tells them that he has in his dorm room Augustine files. Enzo who wants them to listen his side of the story, he becomes quite nervous when they don't listen to him and he demands Damon to stay when Aaron and Stefan leave for the dorm.
Enzo is still mad at Damon for leaving him behind and after a while they start fighting. He throws Damon through a window but Damon tells him he won't fight him back. Enzo informs him about the poison and that he has to kill him but the poison acts quickly on him and he collapses. Damon takes him back to the lab and injects him with everything that writes "antidote" on it. One of them works and Enzo wakes up. Damon explains him how he was able to leave him behind and the prize he paid for it but Enzo doesn't care and he tells him that he will always be a monster.
Meanwhile, Stefan and Aaron arrive at the dorm and Aaron attempts to kill Stefan with one of the vampire weapons he has there. Stefan realizes his intentions and he stops him but before he kills him Aaron tells him the rest of Damon's story and how Damon killed all his family members for generations just to revenge. Stefan, after hearing Damon's revenge plan, lets Aaron live saying that not all vampires are like his brother. Stefan turns to leave but Aaron gives him all Wes' files before he goes. In the meantime, Wes keeps Elena in the basement of her father's old medical practice. She wakes up and Wes informs her about her father's experiments and Elena stars having some memories of her as a little girl with her father. Despite the tortures she remembers that her father was doing all these to help people, for example to use the vampire blood as a cure to many diseases.
Wes prepares to inject Elena with the serum that will make her crave for vampire blood instead of human blood, but before can do it, Stefan arrives and saves her. Elena gets her father's journal before they leave and Aaron comes later on the basement finding Wes unconscious. He wakes him up and tells him that he is not helping people with this research and he is also furious at him because he sold him out to the Salvatore brothers without caring for his life. He tells him that he doesn't want to see him again and he leaves taking with him the syringe that contains the serum that Wes was going to inject Elena with.
Back at home, Elena reads her father's journal while Damon comes in and is mad at her because she defends him all the time, no matter what he has done in the past and how horrible it was. He tells her that he can't change and he doesn't want to change her so he breaks up with her.
In the meantime, Katherine decides to solve her problem by working out and he asks Matt's help. Matt calls Nadia who's mad at Katherine for trying to kill herself without saying goodbye. Katherine asks about forgiveness and Nadia has a plan that might help Katherine; to put her spirit into another body like a traveler does. Katherine declines her offer because she likes her current body and Stefan likes it as well. Nadia realizes that the forgiveness Katherine asked was about Stefan and not her and she leaves disappointed. Before she leaves, she meets Matt and asks him to hold onto the traveler's knife in case Katherine changes her mind. Katherine does change her mind after a conversation she has with Stefan that makes her think that there is yet hope for a relationship with him and at the end of the episode she calls Nadia to tell her she has changed his mind. She wants to make the exchange but before she gets out of the house she has a heart attack and collapses.
- 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.
- Damon and Elena 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 Greyson Gilbet's basement of his medical Clinic.
- Mystic Falls
- Whitmore College
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
- 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."