Caroline had the largest number of serious relationships in The Vampire Diaries. She managed to have romantic chemistry with the majority of the cast, and there were moments throughout the series in which each of her partners felt like the perfect fit.
As different characters developed and regressed, it became easier to decide who Caroline's best love interests in The Vampire Diaries were. Despite the heavy focus on her romances with them, neither Tyler nor Matt make the top of the list. There are several ways that both men could actually be considered the worst boyfriend Caroline ever had.
Tyler: He Didn't Trust Her
Trust is vital in any healthy relationship, and there had always been a serious lack of it on Tyler's end. Caroline was the only person Tyler could turn to after he triggered the werewolf curse, and she was there for him through every stumble and fall.
She risked her life to help him during his first transition, but Jules still managed to turn Tyler against her. He became convinced that Caroline killed Mason, and he trusted Jules instead of the person who had his back from the start.
Matt: He Hated Vampires
Matt's personality can be perfectly summed up with his hatred for vampires in the latter half of The Vampire Diaries. His life was constantly put in danger by supernatural creatures, but they're also the reason he made it out of the show alive.
He developed a bias against all of them, and let it overshadow his love for his friends. Matt hated what Caroline was too much to see past it, even though vampirism made Caroline a stronger, more independent version of herself. It's ironic, because the rest of her love interests had no regard for Caroline until after her transition.
Tyler: He Let Brady Torture Her
Aiding and abetting in Caroline's kidnapping is one of the worst things Tyler has ever done. It might not have been his plan, but he let Jules and her boyfriend torture Caroline because he falsely believed she betrayed him.
Caroline only kept the information from Tyler to protect her other friends, and she proved her loyalty to Tyler on several occasions. Yet, he still let Brady torture her, and was hesitant to unlock her cage. Tyler was prepared to let Jules kill Caroline, and she only made it out alive because Dr. Martin came to the rescue.
Matt: He Constantly Belittled Her
Caroline deserved someone who realized how incredible she was, and Matt flat out admitted that he never liked her. There's nothing wrong with relationship development, but Matt never stopped throwing around insults that would hurt anyone's self-esteem.
Matt had a superiority complex when they were together, and he seemed to think he was out of Caroline's league. He chose to take everything Caroline said far too literally and constantly made her feel bad about herself.
Tyler: He Left Town Without Saying Goodbye
Given everything he put Caroline through, Tyler leaving town could be considered a positive thing. But Caroline doesn't give up on people, and no matter how angry she was at him, she still cared about Tyler.
He didn't do anything to warrant her forgiveness or fix their friendship, and he left Mystic Falls without even saying goodbye. Caroline was never going to accept his apology the same night he put her through such a traumatic ordeal, but he didn't stick around to try to make it up to her.
Matt: He Never Thought Their Relationship Would Work
Matt was certain that his and Caroline's relationship was doomed from the start in The Vampire Diaries, which should've been a red flag. He wasn't wrong, but he didn't recognize that he was the more problematic of the two.
It's questionable why Matt would continue to date Caroline with such a negative mindset, as it seemed like he didn't want things to turn out well. Matt told Caroline they would never work immediately after he kissed her, and while Caroline didn't seem to put much stake into the statement, it's a mood killer.
Tyler: His Jealousy Was Oppressive
The moment Klaus expressed interest in Caroline, Tyler and Caroline were a means to an end. Caroline and Klaus do have some of the best moments in The Vampire Diaries, but her feelings for the original hybrid aren't what destroyed their relationship.
Tyler had plenty of reasons to hate Klaus, and his interest in his girlfriend was the straw that broke the camel's back. He could barely contain his rage when he saw them together, and there were several instances when Tyler took things too far. Klaus wasn't hiding his love for Caroline, but all Tyler had to do was trust Caroline when she told him not to worry.
Matt: He Worked Against Her With The Sheriff
Matt spent the majority of The Vampire Diaries Season 2 lying to Caroline and feeding information to her mother. It was clear that Liz was waiting for the right time to stake her, and Matt helped by keeping up his charade for far too long.
He secretly drank vervain and asked Caroline to make him forget she was a vampire, which was a part of his plan with the sheriff. Caroline had no idea her mom and boyfriend were plotting to kill her, and while Matt eventually comes around, it doesn't make up for his past actions.
Tyler: He Chose Revenge Over Her
Tyler and Caroline's breakup is irrefutable proof that he never loved her in the way she deserved. Even after Klaus let Tyler return to Mystic Falls to be with Caroline, he stayed away. While helping the other hybrids was an honorable thing to do, Tyler made no effort to act like a boyfriend.
It became clear that she was never his priority when Caroline gave him a choice that should have been easy. She asked him to stay and be the love of her life instead of going after Klaus, and he broke her heart.
Matt: He Was Still In Love With Elena When They Were Dating
It's understandable that Matt struggled with getting over his first love, but the way he dealt with it was disrespectful to Caroline. Although Elena had moved on with Stefan, Matt still acted like Elena was the number one person in his life.
Their night out with Stefan and Elena gets uncomfortable due to Matt continually bringing up his and Elena's past relationship. Caroline was left feeling like a third wheel, which is the opposite purpose of a double date.