Mystical convergences often explain the strange occurrences in small towns. While The Vampire Diaries’ Mystic Falls has no real reason to be full of vampires, vampires seem to congregate there nonetheless. The burning of one hundred witches may have something to do with the vampire mecca, though it is not fully explored. Elena and the rest of her friends are free to fall in and out of love with the supernatural people that live there.
Teen Wolf’s Beacon Hills has the Nemeton which explains why Scott always has to forget his lacrosse game and defend the town. Beacon Hill and Mystic Falls have enough supernatural beings to go around so it would make sense that characters in The Vampire Diaries would have a romantic match on Teen Wolf.
Damon And Lydia
Though Damon and Elena fans won ultimately at the series finale the options for Damon’s love life have always been open. He has had a varied history from one of The Vampire Diaries' best villains Katherine Pierce to well-intentioned reporter Andie Star. Damon appreciates all types of women, but especially those who exhibit strength. Lydia Martin does not quite reach the tier of villain but is also not powerless. Lydia is someone who would be able to keep Damon on his toes. He would appreciate her near genius-level intellect and they would be able to converse on the same level.
And while Lydia claims that she doesn't want to be with the “bad guy,” her history speaks for itself. The only non-bad guy in Lydia’s dating history is Stiles. She has dated Kanima and Alphas alike and had a confusing dynamic with Derek’s unempathetic uncle Peter. Damon would not be a large leap to make. Her strength as a Banshee would also ensure that Damon would not have to protect her constantly.
Stefan And Allison
A couple that judges together stays together. Both characters enter situations with the best of intentions but have a moral high ground they prefer to be above. Stefan has his moral high ground because it stops him from becoming a ripper. If he drinks any human blood, he will blackout and become a killing machine. Allison has less of an excuse. She is indoctrinated into a family where they think werewolves are dangerous and should be killed with no exception.
However, these similarities between the two can be used for good as well. As a couple, they would be able to support each other especially when it comes to supernatural beings that should be stopped. But with a relationship with Stefan, Allison would have to re-evaluate what it means to be a monster and be forced to confront her own prejudice.
Elena And Scott
Elena has had dramatic and passionate relationship experiences. Her chosen partners usually require that she profess her everlasting love. And while she may desire danger in her life, what she really needs is understanding and safety. Elena and Scott McCall share many of the same core values. Elena would be a complementary addition to Scott's love interests. They both strive to do what’s right and do not like to morally compromise.
But Scott can also offer danger from time to time. His struggle with his werewolf side often means he encounters conflict. He uses kindness and understanding to resolve these conflicts. Elena can feel useful without having to sacrifice her humanity or worry that her boyfriend is going to kill all of her friends.
Caroline And Derek
Caroline has had a history with werewolf men and has seemed to suit her in the past. She supported Tyler unconditionally. It was only his feud with Klaus that finally tore them apart. This would not be a concern with Derek. Caroline can support Derek but also help him in conflicts where he doesn't lose his free will.
Derek needs someone like Caroline. She is loquacious where he is succinct. But Derek often needs to be told what the right decision is. Caroline’s bubbly personality would make Derek feel less dour. Caroline can also understand his tragic past and family members that may try to betray you.
Klaus And Kate
Klaus and Kate would be a chaotic relationship, but a relationship full of shared ideals, nonetheless. Though neither of these characters is particularly empathetic, they would support each other’s blood lust. Klaus is always out for his own gain, no matter what the cost. His quest to break the curse on his werewolf side involved killing Elena and he didn't care who he had to brutalize to make that happen.
Kate is the same. She is so blinded by her rage towards werewolves that she burned down a house full of innocent people inside. This included human children who were part of the werewolf family. The ends always justify the means with this couple and they would never cast judgment on each other for their actions.
Jo And Chris
Jo’s tenure on The Vampire Diaries was short-lived, but she still made her mark. As a twin from the Gemini coven, she was raised with the possibility that she would be killed. As a teenager, she was put through terrible trauma when her brother Kai gutted her. Jo’s strength and perseverance are something that Chris Argent shares as the head of one of the best families on Teen Wolf.
Chris also had to deal with unhinged siblings with a penchant for murder. Even though Chris is a werewolf hunter, he sees the good in people. He understands that Scott is not only a beast and gives people the benefit of the doubt, just like Jo. This relationship would be a joining of two rational people who may want to distance themselves from the supernatural.
Alaric And Melissa
At some point, Alaric just needs someone normal. All of his relationships have been marred with supernatural interference. Three of his partners have died in one way or another. Both Isobel and Jenna were turned into vampires before their death. Alaric had to also recover from holding Jo as she died at their wedding.
Melissa McCall would offer him stability that he never had. Working as a nurse in the ER, Melissa can handle difficult situations and does not scare easily. She is aware of supernatural beings from Scott should Alaric need to continue helping his supernatural friends. But away from the chaos, they could have a normal relationship doing normal things.
Jeremy And Malia
Jeremy has a penchant for liking supernatural girls. He tried to save Vicki when she turned into a vampire. And he never quite got over his vampire girlfriend Anna who returned to him as a ghost. Jeremy is good-hearted and wants to help in the end. Malia would service that need, but can also defend herself, which is why she is one of one of Stiles' best love interests.
After being trapped in a coyote form for years, Malia had some difficulties adjusting to human life. Jeremy would find her idiosyncrasies charming and have no problem with teaching her how to interact with human beings.
Enzo And Braeden
Enzo and Braeden both have complex relationships with humanity. While trapped in a cell for decades, Enzo lost touch with who he was as a person. He felt abandoned by Damon who left him in the cell to burn to death. But he has a sweet and romantic side to him as well.
This is a dichotomy that Braeden would understand. She is aware of the supernatural, having hunted the Desert Wolf for a long time. This obsession led to her becoming a mercenary. Enzo would never have to worry about her and she could understand Enzo’s penchant for his own obsessions that drive him.
Bonnie and Stiles
The smartest and most capable out of their group of friends, Bonnie and Stiles would be a good match. Both have had to endure supernatural elements that they were not equipped to deal with. Bonnie has both had magic and also had to deal with losing it. She knows how to walk in both worlds. In addition, everyone always depends on her to save the day.
This is a trial that Stiles is familiar with. While he has always remained human, his makeshift pack would be nowhere without him. He always solves the mystery even when the mystery is himself. This couple would have a lot to commiserate about with the shared experience of always being right.