The main characters of The Vampire Diaries all manage to have chemistry with each other. With a few exceptions, almost any two people could be paired together and have a compelling relationship. The couple might not be ideal in the long run, but they still have their moments.

Since there are so many epic romances throughout the series, it’s difficult to decide who each main character should have ended up with in The Vampire Diaries. No one is snubbed when it comes to kissing scenes, and their greatest one isn’t always with their best match.

10 Tyler Lockwood: Reuniting With Caroline In The Woods

Tyler and Caroline aren’t the most popular couple in the series, but it was the only one of Tyler’s relationships that held any real weight. He’s not among the best of Caroline’s love interests in The Vampire Diaries, but she would take the No. 1 spot on his list.

After leaving town to break his sire bond to Klaus, Tyler snuck off to reunite with Caroline in the woods. The line, “You have no idea how much I’ve missed you,” hit especially hard, and it was clear that Caroline was letting his return sink in. Their kiss is bursting with chemistry, and it leads to them hooking up in the old Lockwood cellar.

9 Stefan Salvatore: Finding Out Elena Is In Love With Him

At the beginning of the series, Stefan and Elena’s relationship was especially dramatic. Surprisingly, the theatrics worked for them. Rather than coming off as cheesy, their first “I love you” and sex scene showcased how deep their feelings ran.

The kiss was Stefan’s best because it was full of love rather than lust. He showed Elena who he was physically and emotionally, and he was met with unconditional acceptance. It could be argued that this scene was the most beautiful one of the series.


8 Bonnie Bennett: Playing The Guitar With Enzo

Technically, Bonnie had a slow-burn romance with Enzo that was drawn out longer than Delena’s. The downside was that viewers didn’t get a chance to experience the buildup in the here and now.

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The timeline jumped back and forth between the past, present, and future, and their relationship was like putting together pieces of a puzzle. Fans did get to see their first kiss eventually, and it blew every other kiss Bonnie had out of the water. The actors did an especially wonderful job at showing that there was love between them far before they acted on it.

7 Jeremy Gilbert: Getting Another Chance With Anna

Anna and Jeremy’s relationship lasted for less than half of a season, but it feels like much longer than that. Quality is more important than quantity, and none of Jeremy’s other love interests can come close to what he could have had with Anna.

Fans thought Anna was gone for good after her death in The Vampire Diaries season 1 finale, but she returned as a ghost that only Jeremy could see. He was dating Bonnie at the time, but he admitted to Elena that it was always Anna he loved. Jeremy had been robbed of the chance before, so it was bitter-sweet that he got to kiss her one last time.

6 Damon Salvatore: Realizing Elena’s Love For Him Is Real

There are many scenes that prove Damon and Elena were soulmates in The Vampire Diaries, and this one makes the top of the list. No matter how many horrible things he had done, Damon’s unrequited love for Elena forced viewers to sympathize with him.

He was rejected by the only two women he ever loved for his little brother, and Damon came to accept that he would never find true happiness. The sire bond was like a slap in the face, as Damon finally had everything he wanted only for it to be a cruel joke from the universe. When Damon realized Elena’s love for him was real, it was the first time he was able to kiss her with complete certainty.

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5 Alaric Saltzman: Trying To Compel Jo

Because it’s a teen drama, the original series focused more on the high schoolers’ relationships. Alaric’s romances were lackluster in comparison, but he still had plenty of cute moments and a decent number of love interests.

Alaric didn’t have the same intensity with Jo that he did with Jenna, but Jo was his best kiss. He tried to compel away the night’s disastrous events and Jo’s developing feelings for him. But Jo was on vervain, and she disregarded everything he said to her. When she kissed him, Jo proved that she wasn’t scared of dating a vampire.

4 Caroline Forbes: Being Honest With Klaus

Klaus and Caroline’s first kiss could be considered the most highly-anticipated one, given that Damon and Elena shared their’s back in the second season. This scene doesn’t make up any of the best Klaus and Caroline quotes in The Vampire Diaries, mostly because there wasn’t much talking.

Klaus came back to Mystic Falls for the day and promised to stay away in return for Caroline’s honesty. She later admits she had just planned to kiss him but wasn’t able to stop. Caroline and Klaus have sex in the woods and stay true to their promise of staying away from each other. It’s not until years in the future that Caroline goes to France and tracks down Klaus in The Originals.

3 Katherine Pierce: Putting It All On The Line With Stefan

Katherine had only ever truly loved one person, so her best kiss couldn’t have been with anyone else. She was known for being manipulative, selfish, and untrustworthy, but her feelings for Stefan were proof that she had never lost her humanity.

While she did her best to appear easy-going and confident, spending five hundred years on the run from the man who slaughtered her family wasn’t a fun way to live. Katherine wanted Stefan’s love more than anything, and her selfless deeds led to them sharing their first real kiss since 1864. In fact, this is one of the scenes that prove Stefan and Katherine were soulmates in The Vampire Diaries.

2 Matt Donavan: Rebekah Taking His Place On The Bomb Plate

Matt became increasingly unlikeable the longer the series went on. His hatred for vampires only grew stronger, which was especially odd given that most of the supernatural creatures in Mystic Falls had been his best friends since childhood. Rebekah managed to give Matt a purpose, and his scenes became hollow after she left the series.

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They had a decent amount of buildup, and a romance between them was one that most viewers didn’t see coming. Rebekah and Matt’s relationship development was incredible. He went from wanting her dead to trying to sacrifice his life for hers by staying on the bomb trigger.

1 Elena Gilbert: Trying To Figure Out Her Feelings For Damon

While Damon’s best kiss is in the fourth season, this one is initiated by Elena and far too vital not to pay homage to. Damon and Elena’s previous lip-locks were complicated. The first was a goodbye gift while Damon laid on his death bed, and the second, while epic, was briefer and caught Elena off-guard.

This kiss was the first time she threw caution to the wind and finally let herself act on her feelings for Damon. It was intense in itself, but the lighting and camera angles made the scene look so romantic that viewers forget they were making out in the hallway of a cheap motel.

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