The main characters had a lot of romantic entanglements in The Vampire Diaries, and everyone seemed to have a fling with each other throughout the show's eight seasons. It made things awkward between the characters, as their current love interest was often the ex of a close friend or relative.
Some relationships stayed strictly platonic, and viewers couldn't have been more thankful for it. Not everyone is romantically compatible, which the endless amount of breakups in the series proved. Many of the couples crash and burn, and pairing certain characters together would have only added to the chaos.
Katherine And Matt
Katherine and Elena have a similar taste in men, so it comes as no surprise that Katherine was attracted to Matt. Elena dated him in high school before she met Stefan, but they broke up shortly after her parents' death. Katherine never tried to make any serious passes at Matt, as she was never truly invested in anyone besides Stefan.
If they did become a thing, Katherine would have had to change her ways completely since Matt already hated vampires. But there's no changing Katherine Pierce, and that's part of the reason why viewers love her.
Caroline And Elena
Caroline and Elena work as best friends, but as a couple, their personalities wouldn't mesh well. Because of how close they are, it's easy to forget that Elena and Caroline were frenemies in the first couple of episodes.
Elena thought Caroline was eccentric and acted put off by it, and Caroline felt like she was in constant competition with Elena. They both want completely different things out of a relationship, and while Elena decided to become human, Caroline chose to stay a vampire.
Stefan And Bonnie
Elena and Caroline may have fallen for Stefan, but Bonnie didn't follow their lead. At the beginning of the series, Bonnie respected that Stefan fought his animalistic nature and tried to protect others rather than harm them.
However, they were only friends because they were in the same circle, and they wouldn't have anything personal to talk about if they were left alone. Stefan and Bonnie both have a strong moral compass, but they're one of the few duos in the series that never clicked.
Elena And Klaus
Unlike the Salvatores, Klaus was never in love with Elena. For the entirety of his time on The Vampire Diaries, he only had eyes for Caroline and wanted to use Elena as a human blood bag. It would have been an interesting twist if Klaus was interested in the person he had to sacrifice, but it would have been overkill.
Klaus falling for Caroline because of her bright personality and eternal optimism was much more entertaining than another vampire falling for Elena Gilbert. Elena's love life was complicated enough, and throwing Klaus into the mix would make things too messy.
Bonnie And Kai
A lot of fans were fond of the antagonism between Bonnie and Kai, but in reality, it would never work out. It was entertaining to watch them bicker, but Kai is too over-the-top and unfeeling for Bonnie to handle.
They would be yelling at each other constantly, and throughout Kai's time in the show, there was rarely anything that they agreed on. Kai was also the reason Bonnie was trapped so long in the prison world, and that's something that would haunt her for the entirety of their relationship.
Jenna And Damon
At the beginning of the series, Jenna thought Damon was "ridiculously hot." Damon didn't care much about other peoples' opinions of him, but for some reason, he always wanted to get on Jenna's good side. Jenna developed a disdain for Damon due to his interest in her niece.
There was an age gap between Damon and Elena, but Jenna wasn't aware of just how big it really was. Even getting Jenna to tolerate him was a challenge, so it's difficult to believe that they would ever reach a point where they could have a healthy romance. Additionally, Jenna was Alaric's girlfriend, and Damon was his best friend.
Enzo And Lily
Enzo had always been in love with Lily and falsely assumed that she felt the same way about him. Watching Enzo pine over Stefan and Damon's mother was bizarre, especially when the two had no chemistry whatsoever.
It would be uncomfortable for everyone, especially the Salvatore brothers. While it's difficult to see Enzo in pain, Lily had to shoot him down to set him free. If Lily and Enzo had become an actual couple, he never would have fallen in love with Bonnie.
Stefan And Lexi
There are viewers who saw romantic potential between Stefan and Lexi, but because they had a familial bond, it was weird to imagine them as a couple. They were best friends for over a century and acted more like siblings than anything else.
A relationship between them would feel unnatural, and their close friendship is what made their dynamic so incredible. They weren't afraid to call each other out when necessary, and the fact that they never had a romance made their connection more authentic.
Katherine And Bonnie
At one point or another, all of the characters warmed up to Katherine, even if they went back to hating her a week later. But Bonnie stood her ground and never believed that Katherine was capable of change.
If Bonnie wasn't willing to see the good in Katherine, there's no way a romance between them could work. In turn, Katherine never had an interest in Bonnie besides using her for her powers, and she even admitted that she preferred Caroline over her.
Tyler And Elena
Tyler was one of the few people that wasn't obsessed with Elena. He had no ill-will towards her, and they were childhood friends, but neither of them was interested in each other romantically.
Tyler and Elena having a relationship wouldn't just be awkward, but it would cause problems between Elena and Caroline. They had both been with Damon, Stefan, and Matt, and Caroline often felt like she was living in Elena's shadow. Elena dating Tyler would add more fuel to the fire.