Malachai "Kai" Parker
Kai was born as Malachai Parker in Portland, Oregon. He was part of a coven of witches, the Gemini, of which his large family was part of. Born as a "siphoner" of magic, Kai was seen as an abomination by his family and treated as such growing up. One day, these negative feelings made Kai snap and he went on to kill his siblings in various gruesome ways, which drew the attention of the Gemini Coven, who then harnessed the power of a solar eclipse and trapped Kai in a purgatory dimension as punishment for his crimes. The isolation caused further harm to his already damaged psyche and he swore revenge to those who "wronged" him. Luckily for him, Damon and Bonnie happened to land in his prison through various circumstances and his chance for freedom presented itself...
Suave, funny and incredibly dangerous and insane, Kai quickly becomes the Big Bad of Season 6 and one of the most memorable villains the series has ever produced. He returns as a secondary antagonist in the final couple of episodes for Season 8 note
- Above Good and Evil: Kai seems to think he is very powerful that he believes that he is above everybody else. He feels that he could use this power to be destructive or hurt others whenever he feels entitled to do so. Kai seems to lack morals and has no idea of right and wrong. Kai doesn't seem to care about hurting others and only seems to care about what he wants and he will do anything and everything in order to get it. It is very clear that when it comes to Kai, morals have no place in his life whatsoever. Even hurting his family didn't seem to faze him.
- And I Must Scream: Kai being trapped for years in a dimensional prison constructed by the Gemini Coven. Later he is tortured in actual Hell when he dies by the Devil. He manages to escape...only to be trapped in a new dimensional prison due to Bonnie, with no hope of escaping. One would feel sorry for the guy...but then again, it IS Kai.
- Aloof Older Brother: To all of his siblings, including Jo, Luke and Liv. Kai has openly said that even though Jo is his fraternal twin sister, Kai is still slightly older than her. Kai is the oldest child in the Parker family of eight children. Kai has said that he grew up with a bunch of little brothers and sisters and that he found them all annoying. In personality, Kai is very aloof, cold and sociopathic andid not fit in with his family. Kai also seems to have the special ability, unlike his siblings, of absorbing magic from other witches. It could be assumed that shall Kai try to absorb the magic from his other siblings or any other witches, then Kai could possibly become the most powerful and the most dangerous character in the series.
- Ax-Crazy: Kai has mentioned that he murdered his entire family is very gruesome ways. This shows that Kai is incredibly sinister, evil and psychologically deranged. He also seems to show no remorse for his heinous acts and in fact, seems to boast about them.
- Awesome Mc Coolname: Come on, he's called Malachai. He even points out at one point that by calling him Malachai, his parents must've expected him to be evil.
- Badass Boast: Kai won't hesitate to constantly brag about how powerful he is and how he has the ability to absorb others witches magic whenever he wants to. Kai has also shown that he is highly arrogant and that he will threaten others without any remorse.
- Bad Powers, Bad People: Kai is extremely powerful, so powerful that he has the ability to absorb magic. Of course, his family thought that because he possessed this ability, he was an abomination. Although powerful, it is obvious that he uses his magic and his abilities to do harmful things to other people. It could be assumed that Kai used his powers to murder his family.
- Belligerent Sexual Tension: Kai seems to have this with Bonnie. Despite the fact that Kai is known to be psychopathic, one can obviously see that Kai is a very flirtatious personality and he often engages in Snark-to-Snark Combat with Bonnie. Even Damon seemed to notice the obvious sexual tension and flirting going on between Kai and Bonnie and Damon managed to get a little bit...jealous. This soon ends quickly when Kai reveals his true colors.
- Berserk Button: Being called an "abomination" by his family managed to set Kai off to the point where he gruesomely murdered his entire family.
- Big Bad: Of Season 6. Kai is so evil that he is possibly irredeemable. He kills without any remorse and he plans on wreaking havoc to innocents if he shall get free of the dimension or hell that he is stuck in.
- Black Sheep: Of his family. According to Kai himself, his family saw him as someone who was an abomination, someone who did not belong or fit in with the rest of the family. This is because Kai possesses the ability of being able to consume or absorb magic. It could be assumed that Kai had intended to use this ability to absorb and consume the magic of the rest of his family in order to become more powerful and dangerous.
- Card-Carrying Villain: Kai makes it known that his intentions are not so good. He openly brags about how he has murdered his entire family with the exception of one of his siblings without any kind of remorse whatsoever. He seems to also revel in power and threatens to use that power to harm others whenever he feels he wants to.
- The Charmer: Despite being evil and sinister, Kai has shown that he can be very flirtatious and charming when he wants to be. He has shown flirtatious behaviour towards Bonnie a few times, indicating that he is a bit of a womanizer as well.
- The Chessmaster: Kai appears to be cold, calculating, manipulative and methodical. He is very sociopathic and will use and manipulate others in order to get what he wants. He also seems to have no problem blackmailing others in order to get what he wants. Kai has some sort of agenda if he breaks free out of his Hell and it is unknown what his true intentions are.
- Comedic Sociopathy: Kai is capable of incredible sarcasm and humor and he is often making a sarcastic or witty comment whenever he wants to. His natural talent for this is a part of his friendly act and he this to get what he wants.
- Con Man: Kai seems to very good at deceiving and conning others in order to get what he wants. He's shown to be strongly manipulative and a good liar, showing no problem with manipulation. He is very good at manipulating and conning that he even manages to put on a friendly facade or act in order to persuade others to do what he wants.
- Dark Is Evil: Kai is only seen wearing darker clothing, in particular, black clothing. It is also obvious that Kai is evil and does not have good intentions whatsoever. He has also proven that he is extremely threatening and dangerous and he is a formidable force to be reckoned with.
- Dark Messiah: Kai is extremely powerful, extremely deadly and extremely dangerous. If he breaks free, it is unknown what kind of trouble and havoc he will wreak. Kai is of an unusual kind considering that he has the special ability of consuming and absorbing other witches magic. Meaning that if he chooses to, Kai can absorb or take the powers of other witches whenever he pleases. Despite the fact that he is very powerful, his family saw him as the opposite of normal and instead, referred to Kai as an abomination.
- Deadpan Snarker: Kai possesses a very dry sense of humour and he can even be humorous and witty at times. Kai is very snide, sarcastic and snarky and he sometimes engages in Snark-to-Snark Combat with Damon. Kai even said that the fact that he was named Malakai makes him seem like he was born to be evil.
- Determinator: Kai has shown that he is a very persistent and determined individual. When he wants something, he will stop at nothing to get it, even if he has to resort to the most evil or underhanded methods or ways to achieve his goals and agenda.
- Dragged Off to Hell: Kai was imprisoned in a purgatory prison or dimension of some sorts after he slaughtered his entire family in many gruesome ways. The Gemini Coven took notice of Kai's highly immoral actions and as a result of this, the Gemini Coven used the power of the solar eclipse and trapped him in the purgatory dimension as a punishment for his horrible crimes. Since then, Kai has been waiting too be released from his Hell so that he can wreak havoc. When he dies at the end of Season 6, Kai is dragged off to literal hell but manages to escape in Season 8...only to be imprisoned once again in a new, more permanent prison, courtesy of Bonnie.
- The Dreaded: If Kai gets free from the purgatory dimension that he is trapped in, it could spell absolute chaos, destruction and hell for the entire town of Mystic Falls, in particular the Mystic Falls gang.
- Evil Feels Good: Kai embraces his evil and villainous acts and behavior. He shows no remorse or guilt for murdering his entire family and revels in his special ability to absorb and consume magic. Kai has also shown that he is capable of being The Corrupter and that he will use others in order to get what he wants. He also brags about how he has murdered his family in the most gruesome ways.
- After absorbing Luke's energies, he inadvertently absorbed Luke's empathy as well, which causes remorse and doubt to now accompany his actions. He soon gets over it in the Season 6 finale.
- Evil Gloating: Kai has bragged and boasted about how he has killed his entire family without feeling any remorse or guilt. He seems to embrace in his evil and immoral behavior and has the intentions of wreaking havoc and causing much destruction, chaos and pain once he is free from his purgatory dimension. Kai has also been seen bragging about how powerful he is and that he has thew ability to consume other witches magic whenever he wants to. He threatens to use this ability on Bonnie a few times in order to intimidate her.
- Evil Is Petty: Has shown that he is incredibly spiteful and petty and that he commits evil and immoral acts because he simply cannot help himself. Kai revealed that he killed and murdered his own family without any sense of guilt or remorse all because of what they thought of him, which was an abomination. Kai seems to believe that his family thought Kai was an abomination because of his special ability to absorb magic from other witches, but that was only half true; it was the fact that he was an evil and sinister person that made his family view him in such a horrible way.
- Evil Plan: Kai plans on using Bonnie and her magic so that he could get free from the purgatory dimension that he was trapped in for his horrible crimes. Kai seems to make it known that he has every intention of causing much chaos and destruction wherever he goes. However, despite the fact that Kai makes it know that he plans on causing trouble, it is not clear what Kai's true agenda or motives are once he gets free. It is a possibility that he could be seeking revenge of some sorts for being trapped and imprisoned.
- Evil Sorcerer: Kai is an extremely powerful witch who possesses powerful abilities. Kai also possesses a special ability which allows him to consume or absorb the magic of other witches. Meaning that he is able to take away another witch or warlock's powers temporarily or permanently.
- Evil Twin: With his sister Jo. Kai and Jo are actually fraternal opposite sex twins. While Jo is seen to be generally kind and caring, Kai is seen to be the complete and total opposite of her, very crazy, psychotic and sociopathic. Jo has a moral conscience while Kai doesn't seem to care about morals and doing the right thing. Kai and Jo are like night in day in terms of personality, temperament and outlooks that is sometimes unbelievable to realize that the two are even related much less twins.
- Evil Wears Black: Kai is seen wearing black clothing, which is fitting, considering that he is the Big Bad of the season. In fact, Kai wears all black clothing.
- Expy: Of Silas. It seems as though Silas and Kai have a lot in common in terms of their characterization. Both have shown that they are evil and have very bad or evil intentions. Silas and Kai are both Affably Evil and can be polite and charming when they want to be. Both Silas and Kai are very powerful warlocks with incredible amount of power. Both Silas and Kai have been trapped in a dimension of some sort, with Silas being trapped or entombed in a cave and Kai being trapped or imprisoned in a purgatory dimension. Although, despite the many similarities between the two, Silas major motivation for his evil acts was true love while Kai's major motivation for his evil acts is pure hatred (against his family). Both Silas and Kai have also been referred to as "abominations". Let's not forget that both Silas and Kai also have a preference for wearing black or darker clothing.
- A Fate Worse Than Death: Trapped forever in a new dimensional prison by Bonnie, listening to a song he hates on repeat for the rest of eternity, unable to die.
- Faux Affably Evil: At first, Kai actually appears to be somewhat innocent and childlike. His physical appearance does not appear to be in any way dangerous or intimidating whatsoever. In fact, he seems like he could be a cute, nice guy judging by first impressions. Overall, Kai seems to lack an evil or intimidating villainous demeanour, however, underneath that innocent childlike boyish facade is a very evil and sinister person who is unrepentantly evil and remorseless. Kai is able to be friendly and charming when he wants to and he even possesses a very dry sense of humour and wit. However, this is the same guy who committed a very heinous act when he murdered his entire family in the most gruesome ways. His friendly and charming facade is all an act and he often uses it to manipulate in order to get what he wants.
- Freudian Excuse: Isolation and being treated differently from everyone else may have contributed to Kai's evil and he sometimes muses that others made him that way and he might as well be evil but he soon proves to others in-universe and out that he actually loves being an evil dick.
- Humanoid Abomination: Kai's entire family had referred to Kai as an abomination, which Kai had mentioned had hurt his feelings. Because of the way his family saw him, Kai slaughtered his entire family without any remorse, feeling like his family made him out to be a monster because of his special ability to consume and absorb magic.
- Jerkass: Kai is incredibly evil and sociopathic and he does not have any redeemable traits or qualities. Kai actually murdered his entire family all because he felt that he was an abomination and he did not take it too well so he ended up lashing out in the worst way imaginable against them. While absorbing Luke's essence managed to briefly fill his heart with empathy, he loses it and becomes himself again after Bonnie traps within the alternate prison dimension, arguably even worse off than before.
- Kick the Dog: Too many to list here but several notable ones include finally murdering his twin sister, Jo, on the day of her wedding before killing off the rest of his family. He comes back as a Hybrid Witch-Vampire and goes on to torture the main cast a couple of more times, especially poor Rick and Bonnie.
- Kick the Son of a Bitch: Does this to Damon by torturing him as much as possible. He even manages to fill bottles of water with vervain in it in order to weaken Damon so that it will be impossible for Damon to ever beat him. Kai also planned on staking him and physically torturing him as much as possible, that is until Bonnie intervenes and stops Kai. Through Kai's actions against Damon, Kai manages to get Bonnie's magic back.
- Magic Is Evil: This is pretty straightforward in regards to Kai. Not only does Kai use his magic to commit horrible acts, but he also has the special ability to being able to consume or absorb other magic from other witches whenever he wants to. Kai has shown that he is highly dangerous and he is not to be messed with.
- Manipulative Bastard: Kai has shown that he is extremely cunning and manipulative. He won't hesitate to use blackmail in order to get what he wants. In fact, Kai is so manipulative that his agenda or what he really wants or plans to do are not even clear. All that is known is that he is trying to manipulate and use Bonnie and get her to use her magic to get himself out of the purgatory dimension that he is stuck in.
- Mr. Fanservice: Come on, just look at him. Although Kai is super evil and doesn't have the best of intentions, one cannot deny that Kai is very attractive and deadly charming.
- Off with His Head!: Kai's ultimate fate in the season finale, courtesy of Damon.
- Oh, Crap!: This is how Kai reacts when he realizes that by torturing Damon, he triggered Bonnie to get her magic back. As a result, he ends up succumbing to Bonnie and stops torturing Damon. Fortunately for him, Kai planned on using Bonnie and her magic to get out of his purgatory dimension that he is trapped in as Kai has said that Bonnie'e magic would be the key for all of them to get out of the dimension.
- Several times in Season 8 when he escapes from Hell and learns that he has to run from the Devil. He gets a final one when he realizes Bonnie constructed a newer, stronger and more permanent dimensional prison of his personal "hell": being strapped to a chair in chains, listening to a song he hates.
- Polar Opposite Twins/Sibling Yin-Yang: With Jo, his fraternal twin sister. Kai and Jo may be twins but they couldn't be more opposite if each other. While Jo is seen to be caring, kind, helpful and has a strong moral conscience, her brother Kai is the total opposite of her in terms of personality. Kai is very sociopathic, murderous, crazy and unpredictable. Kai also seems to have serious anger issues and exhibits very troublesome and crazy behaviour, especially when he is provoked to anger. Jo is also a doctor which also implies that Jo likes to help people and save them as well. Kai is the opposite in the sense that he seems to take pleasure in torturing innocent people andalso killing with no remorse whatsoever.
- Shipper on Deck: Seems to be one for Damon/Bonnie. He realizes that despite the fact that the two constantly argue, snark and yell at each other that on some level, even if Damon and Bonnie both don't want to admit it out loud or to themselves, they have a deep affection for each other. Kai had realized that through possibly killing Damon, Bonnie received her magic back and saving Damon's life when it was in danger was a motivation for her to get her magic back. Kai said that Bonnie would always come back for Damon no matter what because "that is how they show their love".
- The Sociopath: Kai has shown that he has zero remorse or guilt for all of the horrible things that he has done. He shows that he does not care that he murdered his entire family all because they viewed him as an evil abomination. Kai has also said that he murdered his family in the most gruesome ways and he has shown no guilt over what he has done to his family. It has also been said that his character is irredeemable and therefore has no good in him whatsoever.
- Soft-Spoken Sadist: Kai is not over the top in his mannerisms and he is rather subdued and composed. He seems to have a very calm demeanour and he is very methodical and strategic in the way he acts and the way he thinks.
- Would Hurt a Child: Hurt? Kai murdered his younger siblings gruesomely. In Season 8, after learning that his nieces were in the same building as he, he went after them with the intention of cutting them to pieces with a giant axe. Thankfully he was stopped by Rick and Caroline in time.
Josette "Jo" Parker/Jo Laughlin
Jo is a tough and accomplished doctor at Whitemore University hospital. She is Elena's medical teacher and Alaric's new Love Interest.
It's revealed Jo is the older sister of Luke and Liv Parker and the twin sister of Kai Parker. She is also a witch, but she no longer has access to magic.
- Big Sister Instinct: Protected her little siblings Lucas and Olivia from her Evil Twin Kai, when he attempted to kill them. When the time comes for Luke and Liv to carry out their coven's barbaric 'Merge' ritual, Jo decided to undertake the ritual with Kai so to spare her siblings the horror of having to take either one's life.
- Big Damn Heroes: When Alaric is killed by the Traveler's magic purification border that removed his vampirism which kept him alive, Jo manages to resuscitate him at just the right moment bringing air back into his corpse, saving his life.
- Brought Down to Normal: Jo is a witch, but she has relinquished her magic; she stored it away in a kitchen knife. She later on in the season takes it back so she can train to beat Kai in the Merge ritual.
- Later on, she has to give it to Kai so to help him recover from his faux Merge with Luke (to prevent her death and those of the Gemini Coven).
- Dark and Troubled Past: Jo was part of a large family that were members of the Gemini Coven. She had seven siblings, along with Kai her twin. Kai turned out to be a total sociopath. When he learned he couldn't become the all-powerful leader of the coven because their youngest siblings Luke and Liv were chosen instead, he went on a killing spree. Kai attempted to kill Luke and Liv, gruesomely murdered their four other siblings after gutting Jo in her guts with a kitchen knife, scaring her for life. After Jo managed to hide Luke and Liv, and Kai is Dragged Off to Hell by their father, Jo decided to leave her family and her witch legacy behind to become a doctor.
- Hospital Hottie: While a nurse at the university and good at her job, Jo is noticeably attractive and striking as Alaric is quick to note.
- Long-Lost Relative: She is the older sister to twin witches Luke and Liv. Jo severed contact with her family after Kai went on his killing spree when she was 22.
- Killed Off for Real: It was a long time coming but she's tragically killed by her demented brother Kai on her wedding day, along with her babies.
- Rescue Romance: She saves Alaric her new beau from dying after his vampirism is stripped. The fact that this is also the reason Alaric is changed back to human, and he doesn't have to worry he'll be tempted by her blood when he's with her takes this Up to Eleven.
- Reasonable Authority Figure: Outside the classroom, Jo is shown to be amicable with her students including Elena and Liam. When she discovers that Elena is a vampire, but she saved the life of 'Lady Whitemore' by giving her blood, she allows Elena to stay on as her student and eventually strikes up a friendship with her, even covering for her when needed.
- The Medic: Jo is an accomplished doctor. After Kai's defeat, she chose not to be a witch and went to medical school. She eventually joined the Army as a medic. She now works as a medical doctor at Whitemore University.
The leader of the Gemini Coven of witches and the father of Kai and Jo Parker as well as the twins Liv and Luke Parker.
- Action Dad: Joshua Parker is the all-powerful leader of the Gemini Coven. Should the need arise, he will jump into action to defend himself and those around him from threats.
- Archnemesis Dad: To his son Kai, because he killed four of his other children, and as punishment Joshua imprisoned him for all time.
- Arc Words: "The coven comes before family". Mr. Parker makes it known he believes the needs of the coven come before the needs of his family. This is justifiable as if the leader of the Gemini were to die before a new one was selected, the entire coven would die too, including the family.
- Bitch in Sheep's Clothing: While he at first appears to be a father who cares about his kids, the way he treats them is questionable. He would forcibly push his beliefs of fulfilling their duties to the coven over familial loyalty and other moral obligations on them, such as their Good Is Not Nice mission against the Travelers and completing the Merge ritual even though the residential outcome is one twin becoming the leader and ensuring the coven's future but being responsible for the other twin's death.
- Killed Off for Real: In the season six finale by his son Kai along with all the other Gemini by Kai's suicide so for him to transition into a Heretic vampire.
- The Leader: He is the head of the witch coven Gemini, the source of their power, their most powerful member. Halfway through Season six, the position of leader is eventually taken from him by Kai.
- The Stoic
- Offing the Offspring: Joshua whenever he deems it necessary, he's bold enough to even kill off his children.
- When he learns there is a chance Kai could escape from his prison, he attempts to murder Jo from miles away so Kai wouldn't be able to undertake the Merge.
- After Luke and Liv put their foot down saying they won't do the Merge, he appears compliant - then he constrains them magically so to forcibly perform the ritual himself unto them.
- Outliving One's Offspring: When he first appears, you feel for him because four of his eight children are dead - at the hands of another, except ... see Offing the Offspring above.
A young woman Stefan started dating before the start of Season Six. She is later turned into a vampire by Enzo.
- Animal Motifs: She loves dogs.
- Cassandra Truth: When she asks to know more about Stefan, he tells her he's a vampire. She believes he's joking and scolds him.
- Kick the Dog: She tells Stefan it's her fault she's now a vampire when Enzo is the one who turned her. Caroline was going to teach her how to be a vampire, but Ivy wants to go to a party and snaps her neck.
- Killed Off for Real: Captured by Tripp Cooke and is killed by being transported by him in his vampire-proof van over the Travelers' anti-magic border.
- Neck Snap: By Enzo. Turns out Enzo actually turned her into a vampire.
- Replacement Goldfish: Ivy is this for Stefan when he tries to turn his back on his old life in Mystic Falls after Damon's death in Season 5.
- Too Dumb to Live: She fed on a human victim losing control of her bloodlust. Her face was covered in blood. She didn't wash it off and ran right into Tripp Cooke which led to her death.
A cancer patient who is on the verge of death at Duke University hospital. He is given vampire blood by Caroline in an attempt to cure him.
- Curse That Cures: Averted as Caroline's vampire blood doesn't cure his cancer. Because cancer cells grow, the blood enhances his tumors killing him. After transitioning into a vampire, the cancer has also been enhanced to Stage 10, a level of cancer that doesn't even exist. The resulting tumors caused him pain, he could hear his tumors growing.
- Hope Spot: After Caroline gives him her blood in an experiment, it appears to work allowing him to walk around. She is overjoyed, convinced she can save her mom ... until Colin actually dies later on from the blood speeding up the cancer.
- Mercy Kill: By Damon.
- We Hardly Knew Ye: He is killed off in the episode after his intro.
Tripp Cooke (born Thomas Vincent Fell III)
Tripp Cooke, born Thomas Vincent Fell III, is the head of Mystic Falls new militia community in Season Six whose trainees include Matt Donovan. Tripp is determined to protect his town at all costs. He is also a vampire hunter.
- Anti-Hero: Of Type IV.
- Badass Normal: When he's not training his community militia, Tripp hunts down vampires - one has to be a badass in order to do so.
- Big Bad: Of the first seven episodes of Season Six.
- Embarrassing Nickname: He changed his name from Thomas "Tripp" Vincent Fell to Tripp Cooke with the given explanation below."My dad called me "Tripp", I was such a clumsy kid that . . . I took my mom's maiden name when he bailed - I mean could you imagine? Tripp Fell?"
- Fate Worse than Death: Tripp is firm in his believe that being a vampire is worse than death.
- A Father to His Men: Tripp serves a surrogate father figure to his young militia trainees.
- Hoist by His Own Petard: Tripp uses the Traveller witches' Magic Purification Spell over Mystic Falls to exterminate vampires. Guess what Enzo does to deliver some comeuppance on Tripp for trying to kill him? See Karmic Death and Karmic Transformation below.
- It's Personal: His wife Kris was killed by a vampire right in front of him. Futhermore the vampire compelled him to think she died of a car accident which was his fault. His crusade against vampires has shades of this.
- Karmic Death: When Tripp crosses over the Magic Purification border, he suddenly dies via slit throat, revealing he'd been transformed into a vampire.
- Karmic Transformation: Tripp was transformed into a vampire by Enzo, the very creatures he hated.
- The Lost Lenore: His wife Kris was killed by a vampire.
- Shed the Family Name: Tripp's from the Founding Families, the Fells. He took on his mother's maiden name after his father abandoned him.
- Slashed Throat: How he's killed off-screen courtesy of Enzo for his Karmic Transformation into a vampire.
- What the Hell, Hero?: After the Mystic Falls vampires capture him, his own men hold Sheriff Forbes hostage. Matt calls him out on this.
A young woman who arrives in Mystic Falls in search of her family. She is actually a con artist.
- Asshole Victim: Manipulates and lies to Stefan without realizing he's onto her which leads to Enzo killing her.
- Dark and Troubled Past: She bounced from foster home to foster home until she turned 18 and came to Mystic Falls.
- Friends with Benefits: With Jeremy.
- I Am Who?: She arrives to Mystic Falls to find out more about her family. She's lying because she looking into Sara Salvatore's birth family who's identity she stole. It's all part of her scheme though.
- Killed Off for Real: By Enzo.
- Little Miss Con Artist: She introduces herself as 'Sara Salvatore', the daughter of Stefan and Damon's distant nephew Zach. It isn't until episode 9 she's outed by Stefan and she reveals to him her real name, Monique.
- Ms. Fanservice: Jeremy is quick to note she looks hot in a bikini in episode 3 of Season 6.
- Neck Snap: How she meets her end at Enzo's hand.
- Oh, Crap!: When she figures out Stefan has been watching over the real Sara Salvatore in secret and is now onto her.
A pre-med classmate of Elena's and hospital volunteer at Whitemore University. He becomes Elena's new Love Interest.
- Big Damn Heroes: In episode five of season six, he saves the life of an injured girl using a tracheotomy - despite having only read about it - which amazes and impresses Elena.
- Inverted Trope: Liam is introduced as Elena's new Love Interest yet his portrayer Marco James actually ships Damon and Elena.
- It Runs in the Family: According to Word of God, Liam is from a family of doctors.
- Just Friends: After Elena decides she likes him and starts dating him, he learns she is a vampire. Elena then decides to compel him to forget he never liked her, what he's learned because she decides she doesn't care for him as she cared for Stefan and Damon and that they are just classmates and friends.
- Mr. Fanservice: As noted by Caroline.
- Satellite Love Interest: For Elena after she compels herself to forget she ever loved Damon after his Heroic Sacrifice.
- Unwitting Pawn: Becomes this to No Humanity!Caroline when she compels him to 'experiment' on Sara Salvatore - by cutting her open, cut up her organs and pull out her heart.