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Elena Gilbert is the main character of The Vampire Diaries, pictured here on the cover of The Return: Nightfall. She was born in July 1974 in Fell's Church, Virginia. She has golden blonde hair and lapis lazuli eyes flecked with gold. She is the daugher of Elizabeth Morrow-Gilbert and Thomas Gilbert, sister to Margaret Gilbert and neice of Judith Morrow-Maxwell and Robert Maxwell. She is very fond of keeping diaries, and writes in hers all the time (along with another when it gets stolen, a computer log when they are put in the library and a new one she gets).
Elena had always been the queen in her life. She was the most popular girl in Fell's Church, she had countless boyfriends, and everyone knew who she was. In 1987, her parents died in a car crash after she pointed out something shiny in the road, distracting her father. She and her sister Margaret were then looked after by their aunt Judith Gilbert, who moved to Fell's Church to be with them. Growing up, Elena's best friends were Bonnie McCullough, Meredith Sulez, and Caroline Forbes.
In the short story "Matt and Elena: First Date", Elena went out on a date with Matt Honeycutt, her most recent boyfriend before the series begins, for the first time in mid 1990. A fortune teller tells her to beware of a stranger she describes with Stefan's qualities. In the short story "Matt and Elena: Tenth Date - On Wickery Pond", Matt and Elena rescue some children from drowning in Wickery Pond in late 1990.
Elena vacations to France in the summer of 1991 before her senior year.
On September 4, 1991, Elena's senior year at Robert E. Lee high school begins. At school, however, Caroline declares that she is no longer friends with her, Bonnie and Meredith, as she feels shadowed by Elena's popularity and will try to become more popular herself, making her the group's rival. Bonnie also tells the group about her grandmother teaching her about her psychic abilities over the summer. Everyone is caught up in the mysterious new student Stefan Salvatore, and Elena, having recently decided that Matt just didn't do it for her, vows to make him hers. He repeatedly rejects her advances, making her upset. Elena goes to her parents' graves that evening and Bonnie and Meredith join her, and they make a blood oath to do all they can to make Stefan Elena's boyfriend. An unknown force that the Bonnie says is creeping up on them through a trance chases them out of the cemetery, and Elena loses her apricot ribbon. At homecoming, she becomes so mad when Stefan dances with Caroline that she leaves with Tyler Smallwood to hang out at the cemetery. There, she has a vision of falling into Honoria Fell's crypt. To get away from it, she goes further into the cemetery where Tyler tries to rape her, but Stefan saves her and takes her back to his room in the boarding house loft. Elena screams at him, asking why he hates her and ignores her so much, and her reveals that he has been avoiding her because he is in love with her. They officially start a relationship.
While the girls help prepare for the school's Halloween party, Damon, who has been stalking Elena in crow form, finally appears to her as a human in the gym. She is turned off by his creepiness, but it makes it all the more fun for him. Later, Bonnie performs a dumb supper at her house for Elena, to see the image of whom she will be married to. As she invites him to "come in", Damon enters the house and meets Elena once again. Bonnie's dog, Yangtze, is then found dead outside.
At the school's Halloween party, Mr. Tanner, the history teacher, is killed, and Stefan flees the school. Elena chases after him and sees him feeding off of an animal on the boarding house roof. She is so shocked that she falls off, but Stefan rushes down and saves her. He takes her back up to his room and explains that he is a 500 year old vampire from Florence, Italy. He and his brother, Damon, had killed each other in a mad battle after the vampire they loved, Katherine, had killed herself over angering them, since she could not choose between the two. Since they both had Katherine's blood in her system, though, they came back to life as vampires, wearing silver rings with spelled lapis lazuli in them to protect them from the sunlight. Stefan had carried Katherine's gold ring with him around his neck throughout the centuries, and came to Robert E. Lee High School to meet Elena because she looked exactly like Katherine. He reveals that he has also had Elena's apricot ribbon, and he and Elena then exchange blood for the first time.
Stefan and Elena know Damon is to blame for the bad things happening in the town, but everyone else blames Stefan, as they started happening when he showed up, and now he can not be found. Elena knows that Damon took him, so she runs out of school in the middle of the day on November 1 and goes to the cemetery to confront him.
Damon and Elena have a confrontation, and that night, Bonnie leads the group to Stefan through a trance, who was down a well. He couldn't remember anything. Later, Elena finds at Bonnie's house that her diary has gone missing, and someone probably stole it. A new history teacher, Alaric Saltzman, takes Mr. Tanner's place, and he invites the students to a party at his house. Damon shows up at the party and taunts Elena, and she finds lines from her diary on purple slips of sticky notes. She eventually overhears Tyler and Caroline discussing how to reveal Stefan's vampirism to the community, which she had written about in her journal.
Damon obtains an invitation into the Gilbert home and comes for dinner with Aunt Judith and her boyfriend, Robert Maxwell. Elena shoves Margaret's new kitten, Snowball, into his face out of anger, knowing that she would get scared. In a trance, Bonnie says that Elena's death is in the house, which she assumes to mean Damon. He takes her blood that night, but she is surprised to wake up fine. Elena later stays over at Bonnie's house, but Damon still gets in and exchanges blood with Elena. She, Bonnie and Meredith break into Caroline's house one night when no one is there and try to exchange Elena's diary with Caroline's own. They hear someone coming, though, and escape out the window, where Damon once again appears to Elena. Eventually, Stefan proposes to Elena, giving her Katherine's ring.
On Founder's Day (November 30), Elena and Caroline take part in the parade and wear 19th century dresses to celebrate the founding of Fell's Church. The group knows of Caroline's plan to read Elena's diary aloud and has given up, knowing there is nothing they can do. However, when she goes to read them, she discovers that she has her own. Elena realizes that Damon had switched the diaries after all, and goes to talk to him about it later. Aunt Judith and Robert appear and Damon Influences them to dislike Elena's engagement to Stefan, saying Damon is a better choice. Enraged, Elena takes Matt's car and heads for the boarding house. As she gets there, however, a huge storm brews behind her, and she can see the silhouette of a large owl flying behind the clouds. The storm chases her all the way off of Wickery Bridge in the cemetery, where she drowns in the frigid water.
Stefan finds her body and brings her back up to land, leaving her with Bonnie and Meredith as he goes to the school's quonset hut and drains the blood out of Tyler and a few other boys. Before he can get to Caroline, she starts screaming and he just Influences her to forget what she saw. Stefan then goes to fight Damon, whom he is convinced is responsible for Elena's death. Meanwhile, Elena wakes up as a vampire due to the presence of Damon's blood in her system, and follows the brothers into the woods.
Having been turned by Damon's blood, Elena is convinced she loves him in her delirious state. Damon, however, takes the situation seriously and has her feed on Matt to complete the transition, and then Influences him to forget. Damon then takes her to Alaric's attic to rest. When she wakes up, she realizes what has happened and goes to church where she witnesses her own funeral from the balconies. Meredith alludes to some false memories in her speech, and Elena wonders if Meredith could think she's still alive and listening. Suddenly, all the town's dogs start to attack their owners. Elena meets up with Stefan and Damon and says allows that there may be a chance that Damon is not behind all of the chaos in Fell's Church. The three agree to investigate what they call "The Other Power" in Fell's Church. Later that night, Elena goes to Meredith's bedroom window and has her let her in. They call Bonnie over and Elena explains everything. Meredith reveals that her grandfather was attacked by a vampire before she was born (to her memory) and that was what made her question the recent months. They agree to help investigate, as well. Bonnie later does a ritual which tells her that they will get through their problems with sacrifice.
Eventually, at another one of Alaric's parties, Meredith reveals in the attic that she has been meeting him after school and discussing what he really is - an experimental psychologhist hired by principal Brian Newcastle to determine what was happening. Later in the book, Elena goes to Matt's house one night and explains everything to him as well, feeling sorry for him. She also makes Margaret get rid of Snowball, since the town's animals are attacking their owners, but doesn't explain anything to her as she wouldn't understand it.
On the night of December 13, when Elena feels like the town's animals attacking their owners will come to a climax, Elena, Stefan, Damon, Meredith, Bonnie and Matt meet in Alaric's classroom as the school prepares for the Snow Ball. Bonnie goes into a trance and brings the group to Honoria Fell's crypt, where Stefan and Damon open the casket, revealing that it goes down to another level. They go down there and the ghost of Honoria reveals herself using Bonnie's power, saying that she (who was also a witch) was the one who was possessing her and helping them. Someone had been disrupting her tomb, which is why she came back. She moves on, though, and everyone leaves except for Stefan, Damon and Elena. A fierce white tiger knocks them unconcious and they wake up chained to the wall as Katherine appears before them, saying she faked her death to get the brothers to reconcile. When that failed, she went back to the vampire who turned her when she was dying, and he shaped her into a sadistic, insane, evil ripper and that she eventually killed him, too, along with many other vampires and humans over the centuries. She attracted Stefan and Damon to Fell's Church after seeing Elena (most likely in France) hoping that they would see her, remember Katherine and reconcile like she had originally planned, but once again they did otherwise and fell in love with her. She had also been Snowball, going into the Gilbert house to spy on Elena and being her death. Katherine was the one responsible for most of the things Elena and Stefan blamed Damon for, such as playing with Vickie Bennett, killing Yangtze and even Elena. This redeems Damon in Elena's eyes and she realizes she loves both brothers. Katherine had grown so powerful that she couldn't cross running water, so she had to go under Wickery Creek through Honoria Fell's crypt. She decided to turn the town's animals against their owners out of sheer rage and now simply wants to torture and kill Stefan, Damon and Elena. As she is describing her plan, Elena breaks free of her bonds and pushes Katherine into the sunlight, tearing her necklace free so that she burns up. However, Katherine had also taken the others' rings and set them aside, so Elena dies, too. Being a new vampire, however, she does not burn. Stefan and Damon also break free of their bonds and Elena makes them promise to make up, be brothers again and look after each other with her death.
Everyone reveals everything that happened to the whole town, Elena is given a proper funeral (in which she truly looks like she is just sleeping) and Bonnie puts Elena's diaries (she had written in a separate one when the original was stolen) in the school library on December 16.
Six months later, Elena, who has stayed behind as a ghost, becomes a sort of guardian of Fell's Church. She appears to Bonnie in visions, but someone else plays with them and disrupts them, making Elena appear as the rotted corpse that her body has become. On Meredith's birthday party at Caroline's house, Elena contacts Bonnie, Meredith, Caroline, Sue Carson and Vickie via ouija board and says that "he" is in the house. Soon, Sue is found pushed out of a window, dead. Bonnie summons Stefan and Damon and the group (which now has Matt as part of the team) investigates once more. Caroline (who has become a friend again) says that with all the drama, she will be leaving for a while. Stefan questions the nature of Sue's death and determines that she was used to trigger a werewolf curse. He does some research and learns that Tyler Smallwood's ancestor Jacob Smallwood was a werewolf, and Tyler would have the gene in him. At graduation, Meredith and Bonnie have a fake fight over respect to Elena, and Meredith says she will be visiting her grave that night. Tyler shows up with the intent to rape her just like Elena, but Stefan and Damon stop him and confront him about what he did. They learn that Klaus, the vampire that turned Katherine, came to Fell's Church looking for revenge for Katherine's death. He helped Tyler become a werewolf by killing Sue so that he could be his minion. Klaus later appears in a vision to Stefan with Elena, who says that he is torturing her spirit. In reality, he mails Stefan Caroline's scarf, and he knows he has to go fight him alone. Still, Meredith, Bonnie and Matt sneak along, rescue Caroline, and send Tyler running off into the distance. Damon, who fell out of the group after Klaus brutally murdered Vickie, also shows up, but Klaus has them all beat. As he is about to kill Stefan, Bonnie screams for Elena. She is able to use Klaus' power to appear, and then to call up the restless spirits of Fell's Church to take Klaus away. Elena heals everyone from their wounds and goes away forever, only to suddenly reappear in a new body created by the restless spirits as a reward.
The Return: NightfallEdit
Elena's ressurection somehow transported Fell's Church 17 years into the future (probably because that was her age when she died) as well as Alaric who, while in Russia, was involved in the happenings there. Elena has reverted back to a childlike state. She can not read or speak English, yet she can speak words of White Power, float, glow, and even has glowing wings occasionally. This only lasts a week, however, and soon Elena is a normal human with just a few differences: Her blood is more powerful than any other to a vampire and it also makes her sexually attractive to them, she can telepathically communicate with other supernatural beings that can, and she still has sets of Wings that she does not know how to use yet.
To celebrate her true return, the group goes on a picnic, minus Damon and Caroline who have been acting strangely (afterwards, they go back to the boarding house and celebrate a Christmas for Elena in the short story Elena's Christmas, since she couldn't celebrate one the previous year). Stefan had been writing down Elena's thoughts in his computer when she could not speak, so Damon, being controlled by the kitsune, adds an entry to it by Stefan saying that he has had to go to the Shi no Shi in order to turn back into a human. Stefan mysteriously goes disappearing, and the group decides to find out why everyone is acting strangely. They are possessed by malach, creatures of darkness that the kitsune can command to essentially control the people they possess.
In the middle of their investigation, Damon goes under their control again and starts harrassing Matt and Elena, trying to get them to kiss and causing unbearable pain to Matt. He eventually takes Elena in his car, but she jumps out as it is driving, injuring herself in many ways. She wanders through the woods until she knows she is somehow going through the same place over and over again. As she settles down, plants begin to wrap around her, making her think she is going to die. However, Damon reveals that the kitsune had taken her to their secret house and put a star ball up to her head - a container of memories that kitsune use. The star ball had the experience of the same patch of land over and over again, as well as the possessed plants. Damon explains that he had stolen the Master Keys that belonged to Shinichi and Misao, the fox-spirit entities that had come to Fell's Church after having seen the huge burst of power from Elena's ressurection. That was how he was able to get into their secret house, as the Keys can simply go anywhere when inserted into a door. He heals Elena but soon becomes possessed again. Elena takes one of the Keys and goes to her house, once again appearing before her little sister when she is supposed to be dead. She tells Margaret to run to her friend Barbara's house, and she does as Elena leaves again with Damon chasing her to the school last year when she was alive, to Caroline's house, to Honoria Fell's crypt. Elena uses her Wings of Redemption on Damon to calm him, and he thinks he is in the 15th century again. She then uses her Wings of Remembrance on him and her Wings of Purification to remove the malach from him. He then flies out of the crypt in crow form while Elena uses her key in a ball of light (possibly Honoria) to go to where Stefan is.
She finds him behind bars where is clearly not being fed, but brings him some black magic wine that she and Damon had discovered when traveling with the keys. The kitsune had captured him and put him in this cell in the Dark Dimension as their legal property. Elena goes back to the boarding house and hides in a tree as she watches the kitsune prepare to kill her friends. She uses her Wings of the Wind to swoop down on them and threatens to cut off Misao's tails. She taunts Elena with clues as to where the keys to Stefan's cell are: In the Silver Nightingale's instrument and Lady Bloddeuwedd's ballroom, but they take some of Damon's memories of being redeemed by Elena as the price for the clues, and also the Master Keys. Eventually, the kitsune leave, and Elena and Damon set out with Matt, who is wanted for supposedly raping Caroline (who is pregnant from Tyler) to go to the Dark Dimension to rescue Stefan.
The Return: Shadow SoulsEdit
It doesn't take long for Matt to get fed up and leave, but Bonnie and Meredith join Damon and Elena at the end of their trip. They go to a gate to the Dark Dimension at the far end of the country so that the kitsune won't be able to track them. Damon enters the Dark Dimension with the three girls as his slaves, and as they pass through it, they see many beggars whom Elena gives her jewelry to (even giving her engagement ring that protects vampires from the sunlight to a man named John). They also see a fierce vampire whipping a pregnant woman. Elena stops to help her and the vampire almost kills her, so Damon kills him. The others help the slave, and a nearby girl called Lakshmi takes them to a man called Dr. Meggar. As punishment for the unheard of act of killing a vampire and taking his property, Elena is later whipped in public but does not feel much pain. Damon also meets his old vampire friend Sage, who rescues him from a mob for being Elena's owner. The rescued slave eventually tells the group that she is Lady Ulma. A demon wanted to marry her as a child, and when her parents refused to give her up, he killed them, leaving her a vulnerable slave. Everyone helps Lady Ulma get back into her clothes design business, and soon they have enough money to buy back her house and even her fiancee, a jeweler called Lucen.
Lady Ulma helps them prepare for Lady Fazina's ball, who is also known as the Silver Nightingale. Her instrument, however, is her voice. Damon and Elena get away from the crowd and search all over the mansion, eventually finding a little stone fox in one of Fazina's pens. Seeing blood coming from Damon, however, Elena passes out, realizing that he took her pain when she was whipped, and his scars were now bleeding.
Later, the group goes to Lady Bloddeuwedd's ball. Lady Bloddeuwedd is a strange creature who was created at the beginning of time and who was sent to the Dark Dimension for killing her husband. She catches Elena and Damon snooping around and decides to kill them. Elena, however, starts destroying her Star Ball collection and collecting some in bags, making her furious. She finds the other fox in Bloddeuwedd's "nest" and runs out into the courtyard where she finally reaches through to Damon, shattering the boulder that the child Damon is chained to in her mind. On the way to the Shi no Shi, everyone looks at the Star Balls and they determine that they have found Misao's. They uses the foxes, combined to make a ring, to open Stefan's cell. Bloddeuwedd, however, has begun raging upon the whole city. As she is about to dive down onto the group, Elena uses her Wings of Protection, which Bloddeuwedd flies straight into at high speeds, killing her. The group goes into an elevator that will take them anywhere, much like the Master Keys, when they see a white kitsune come up that Stefan chatted with during his time in the cell. He gives the group a bouquet, but then the elevator closes and takes everyone back to Fell's Church. Shinichi appears, but he is fought off. Damon opens the flower inside the bouquet the next morning, not knowing that it contains a spell to make vampires human again. During her journey in the Dark Dimension, Elena got closer to Damon and realized that she loved him just as much as she loved Stefan.
The Return: MidnightEdit
Determined to be as strong as before, Damon goes to the Dark Dimension using Misao's Star Ball to seek out M. le Princess Jessalyn D'Aubigne, said to have the bluest blood in the land, and eventually gets her to turn him back. However, he accidentally takes Bonnie with him into the Dark Dimension. Elena and the others defend Fell's Church as it falls further into desecation and becomes a warzone. Eventually, the kitsune show up and they are able to take Misao's Master Key in her weakened state. Elena and Stefan go to where Bonnie is (in Lady Ulma's house) while Meredith, Matt and Mrs. Flowers relocate to Matt's house as the malach are destroying the boarding house.
Elena is infuriated with Damon for all of the things Bonnie has had to go through, but is happy to see Lady Ulma's baby, as about a year has passed in the Dark Dimension. Stefan, Elena, Damon and Bonnie go on a journey to the Netherworld, the next lowest world under the Dark Dimension, based on a vision Bonnie had. The Kitsune Treasures are supposed to be in the Netherworld, and one of them is supposed to be the largest Star Ball in existance, which they hope to use to save Fell's Church. When they finally get there, they see Sage, the gatekeeper. They could only choose one prize, so they choose to look for the Star Ball. The door takes them to one of the Netherworld's moons, called the Dark Moon. A tree on the moon has its branches spreading out over the entire skyline as wide as the eye can see. The group starts searching for the star ball, but Shinichi eventually appears, saying that he had to fuse with Misao because she was so weakened by Damon using her star ball. He regrets working for "her" and then dies, because kitsune cannot regret.
Meanwhile, Matt, Meredith and Mrs. Flowers figure out that Isobel Saitou's (a girl they went to school with) grandmother is really Inari, the kitsune goddess, having forced the family to pretend she was related to them for ten years, attracted to Fell's Church due to the intersecting ley lines underneath it. They go to face her down.
When the group at last finds the star ball, it is on some branches. Bonnie tries to get it, but the tree, enchanted to keep vampires away from it, comes to life and stakes Damon. Infuriated, Elena uses her Wings of Destruction, exploding absolutely everything - every little blade of grass, the entire tree that covered the whole moon and of course, the star ball, the liquid inside it evaporating. Inari immediately shrivels up and dies just as she is about to kill Mrs. Flowers.
Elena, Stefan and Bonnie escape the ash covered moon, leaving Damon's body behind. Sage takes them to the kitsune paradise, another one of the treasures, to heal, as Elena had passed out. Since only one treasure may be taken, though, that breaks the rules, so Stefan decides they should take as much of the treasures as they can so that they could meet with the Guardians. They do so and the Guardians do come to arrest them, taking them up to the Celestial Court. It is there that they reveal that they were the shiny object Elena saw when her parents died - they were causing the car to crash so that Elena would die and they could bring her back to life as a Guardian. Her skills at being one were already so good, however, that she saw them and pointed them out, changing everything and causing her parents to die instead of her. This also explains why she was such a good Guardian of Fell's Church in Dark Reunion.
Elena pleads with the Guardians to accept the stolen kitsune treasures and the Master Keys as a trade for restoring Fell's Church as if nothing bad had ever happened to it in the past year. They agree to it, but they can not bring back Damon, as he has already moved on. Infuriated, Elena almost uses her Wings of Destruction, but the Guardians quickly remove all of her Wings (and her telepathy as a result) and then send everyone back to a restored Fell's Church where everyone accepts that Stefan is Elena's boyfriend, no one ever died (Mr. Tanner was just injured, allowing Meredith to still meet Alaric) and the year is 2009, and there is nothing wrong with that. However, Elena unknowingly kept a bottle of the Fountain of Youth, one of the kitsune treasures.
The Hunters: PhantomEdit
Returned to her normal life at home with Judith, Robert and Margaret, Elena finds that Caleb Smallwood, Tyler's cousin, has been working for the family over the summer. She and the others go meet Alaric at the train station where Celia is nearly killed. Everyone tries looking for what could be causing the danger that seems to follow them all, and Bonnie goes into a trance in which she says that Elena brought it to Fell's Church.
Up to this point, Damon had appeared to Elena in dreams at places that were important in their relationship (Lady Bloddeuwedd's courtyard, where she freed his inner child, the school gym, where they first met, and Alaric's attic, where he brought her after she became a vampire). One night, Damon appears to Elena in the flesh, having been brought back to undeath by the drops of the life force from Inari's Star Ball raining down upon him. He tells her not tell anyone about his return until the time is right, though.
Stefan eventually sees Caleb and Elena together in the cemetery and throws Caleb against a tombstone under the idea that he is evil and has caused all the trouble, causing Elena to take him to the hospital. Stefan tries to prove it to her by taking her to Caleb's shed, where they see a pentagram on the floor and objects (such as photos or newspaper articles) from both realities. Stefan and Elena come to the conclusion that the Guardians must have simply changed the look of these things in peoples' minds, but Caleb's clear supernature as a sort of spellcaster allowed him to possess some of the fake memories as well as some of his real ones, making him confused.
Later, Bonnie is found comatose in the Boarding House. Elena tells this to Damon and he lets darkness consume him, making him comatose as well (in crow form so no one notices). While out shopping with Stefan, Elena becomes jealous of the people she went to school with who have completely normal lives, and the darkness overtakes her as well. She awakes in the field of flowers that can hold spells (like the one the white kitsune gave Stefan), one of the kitsune treasures, and sees Bonnie. Matt joins them shortly thereafter, having been taken while he, Meredith and Stefan were confronting Caleb. Caleb only wanted to turn everyone against each other with his spell, hoping that he could get them to confess what happened to Tyler (he knew they were up to something after connecting the mysterious events in his memories), and Meredith told him they truly didn't know. Matt, Elena and Bonnie search for the way out and eventually end up in the nexus room of the kitsune treasures. They go onto the Dark Moon and find Damon battling a giant blue misty woman.
The woman is one of the original phantoms, imprisoned on the Dark Moon by the Guardians at the beginning of time. A phantom is a being that feeds off a certain feeling, but the originals can actually take form, and Elena destroyed their prison when she used her Wings of Destruction. They join in the battle to help Damon.
Meanwhile, Stefan, Alaric, Celia and Mrs. Flowers do a spell to summon the phantom. It arrives in the boarding house garage with Elena, Bonnie, Matt and Damon. Their physical bodies disappear as they have moved back into them. This particular phantom feeds off of jealousy, and it became quite healthy after Caleb amplified it among the group. Everyone casts their jealousies away to weaken the phantom and they set it on fire. The fire doesn't help, so Elena reaches into its solid heart and rips out the rose inside, killing it. Damon gives her blood to heal her burns as fire trucks arrive and put out the garage.
The Hunters: MoonsongEdit
Elena goes to Dalcrest College and gets a bedroom for three with Bonnie and Meredith. Stefan also attends the college, having Influenced the school to accept Meredith and Matt, and Damon lives in an apartment off campus. Elena's History Of The South professor, James Campbell, says that she may talk to him about her parents any time she likes, as he knew them when they went to Dalcrest together.
Students soon start to disappear from campus or turn up dead, and the core group starts investigating.
One night, Damon invites Elena to go out with him as friends when she is waiting for Stefan to be done with a study group, so they do so, but Elena forgets about Stefan. He eventually finds them and asks Elena why she never answered his calls, and she realizes she had forgotten to check her phone. Stefan and Damon begin arguing over her and, pushed to the breaking point, Elena declares that she can't be Katherine and destroy the brothers' relationship by loving both of them at the same time, which had originally driven them to killing each other after they thought Katherine had died because they couldn't accept her decision. She "breaks up" with both of them temporarily so that they can sort out their own relationship, and Stefan obidiently stays away from her. Damon doesn't abide at all, however, and constantly hangs around Elena despite her protests at first. Stefan eventually finds them kissing after waiting a while for her at a party and declares that Damon is not his brother anymore, refusing to speak to Elena until the end of the book.
Elena checks out a picture of her parents in a hall of photos and realizes that they and her professor all have pins in the form a dark blue V. She asks Professor Campbell about them, but he clearly does not want to talk about it. She and Damon research them in the library and think that her parents may have been part of the Vitale Society, a legendary secret society among the students.
Towards the end of the book, Damon invites her over for dinner at his apartment and tells her about the life she could have, traveling the ever-changing world forever as his princess of darkness, collecting riches. Elena realizes that she never really thought it about that way before, and that maybe that was her destiny.
Later, she visits Professor Campbell's house at night and demands to know the the Vitale Society is, knowing that they are connected with the trouble on campus. The professor reveals that back when they were in college, it was far different than what it is now, and he does not know much about what it is now. Back then, it was just about peace, love, and nature worship, until one day, a male Guardian came by and said that there needed to be a new type of Guardian - one that would watch over the Earth by actually living on it. He chose Elena's parents, who had already loved each other, to create the Guardian with the deal that she would be given up at the age of 12. However, they loved her too much and refused to hand her over when the Guardian contacted them again, so the decided to forcefully take her. However, when Elena pointed them out, everything changed and her parents ended up dying instead of her. This story makes Elena question her humanity and wonder if the Guardians intend to give her back her Wings at some point (it is also a possible explanation as to why Margaret seems to remember the first seven books). The professor also remarks that he wonders if it is no coincidence that Elena herself is at Dalcrest now (it is also interesting to note that she specifically asked the Guardians to get her into Dalcrest) and that she may have a destiny to fulfill here. Elena decides to keep this story a secret to herself for the remainder of the book.
Later that night, Matt rushes into Elena's room wearing a black cloak, saying the Vitale Society is behind everything. They had initiated him at the beginning of the year and had created an army of "perfected" people that the leader, Ethan, is now turning into vampires. Stefan substituted himself to free Matt, so he, Elena, Meredith and Bonnie all go get Damon and then go to the secret entrance in an office in the library. Matt and Bonnie wait in the office while Damon, Meredith and Elena go down the trap door. Damon and Meredith fight off the vampires as Elena rescues Stefan, telling him that she may love Damon, but Stefan is her one true love, which she had become even more sure of after having a full-fledged relationship with Damon in Stefan's absence. They make up and defeat everyone, going back up to the office. Stefan explains what Ethan had told to him, that he met one of Klaus' "descendants" in Europe over the summer and had her turn him. She told him all about Klaus and the Salvatore boys, whom she had heard of. He then wanted to ressurect Klaus, but he needed blood from a certain amount of his descendants to do so (this may have been what Cristian was trying to do). He successfully collects both Stefan's and Damon's blood during the brawl. Meredith and the brothers decide to go around campus and take down the escaped vampires as Elena goes back to her room and gets some sleep for the night.
- Elena is 17 in the original trilogy and Margaret is 4. Margaret is still 4 in The Return: Nightfall and Elena is "almost eightteen". However, a few days later in The Return: Shadow Souls, Elena states that she is eightteen. Margaret is 5 the next time Elena sees her in The Hunters: Phantom. In The Hunters: Moonsong, it is revealed that Elena's parents died when she was 12. However, given that Margaret was already born, this would have been right around the very end of her being 12, right before she turned 13, and Margaret's birthday would have come before hers. This would place both their birthdays in the few days between Nightfall and Shadow Souls, which also means that Margaret was literally just born a few days prior to her parents' deaths.
- The circumstances of Elena's death and transition on the TV show mirror that of her book character. They both drive off of Wickery Bridge in Matt's car towards the end of the first semester of their senior year and drown due to a blonde vampire.