ByPri Figueiredo, writer at
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Pri Figueiredo

If you've ever been on a date, then you know just how terribly annoying a third wheel can be. But if you've been the said third wheel, you had - without a doubt - the worst night of your life. If under normal circumstances having a friend tag along on your much-awaited dream date can get a bit disconcerting, imagine having your ex coming along for the ride - and no, I do not mean it in a kinky way!

The Vampire Diaries' main cast has been narrowed down to seven characters for its last season. Although Mystic Falls does seem to be a fairly small town, the characters always seemed to gravitate towards the same people when it comes to their love choices. And that's not even mentioning the Stefan-Elena-Damon triangle - which had its devastatingly odd moments, but eventually culminated with Elena choosing her favorite Salvatore brother. Here are three other times in which living in Mystic Falls and being in love meant putting on the occasional poker face.

3. Beremy vs Anna

Jeremy Gilbert started off just as Elena's little brother, but he soon took on the role of Bonnie Bennett's sweetheart. Jeremy had been around - making out with Matt's sister and falling in love with Anna - before the Bennett witch took his heart. The couple began their romance in Season 2 and they seemed to be the most normal couple to inhabit Mystic Falls, until the supernatural intervened - of course!

When Jeremy found out he was a medium who could communicate with ghosts, he started to talk to his former girlfriend Anna - who had been murdered - while he was still in a relationship with Bonnie. Although the witch tried to accept Jeremy's involvement with Anna, she broke up with him after finding out he kissed Anna's ghost. Let's just say that being cheated on by Jeremy with a ghost was more than Bonnie could handle.

2. Steroline vs Elena

After a long on-again, off-again relationship, Stefan and Elena finally parted ways and she went on to date his brother Damon. A broken-hearted Stefan found a new bff in Caroline, and things slowly evolved into a much deeper bond between them. Steroline began to leave the friendzone when Stefan was being hunted by the Travelers, and Caroline and Stefan fell asleep together in a wrecked car. They might have been just friends then, but that was the spark that kindled their romance.

Needless to say that things got a bit weird after they shared their first kiss - and Elena found out about them - but Caroline's own emotional conflict put hers and Stefan's happily-ever-after on pause. Soon after, Elena was put under a spell by Kai, and it was by her bed at the hospital that the most awkward moment of their triangle finally happened, as Stefan talked about what Elena meant to him and confronted Caroline's feelings for him.

Before we get to our number one, here's a quick bonus for y'all!

Klaroline vs Tylorine vs Hayley

There's a lot of ship names up there, but bear with me here! This one was not a triangle per se - since it had many more than three people involved - but it was still one heck of an awkward moment forged in the name of love. Basically, Tyler and Caroline were together, Klaus liked Caroline and Tyler had a one-on-one time in the Appalachians with Hayley. Eventually, Tyler's little adventure with Hayley was - accidentally - revealed by Klaus to Caroline, and we were all team Klaroline there (at least for a while!).

1. Katherine vs Salvatore Brothers

When The Vampire Diaries took off, Stefan and Elena fell in love and Damon was all about getting Katherine Pierce back from the dead. Both Salvatore brothers had been turned into vampires by Katherine - who was Elena's doppelganger - and both were madly in love with her. She took her time playing both Stefan and Damon to her advantage, alternating her love between them for a whole century.

Eventually, she was entombed in Mystic Falls and Stefan was able to move on (at least a bit) but Damon was relentless in his quest to set her free. He finally succeeded but, much to his disappointment, Katherine broke their little triangle of love when she stated - in a crushingly honest way - that she had never loved Damon.

As Hayley would put it, that's some "teen drama" right there!

The Vampire Diaries closes this next season and, after eight years of keeping Cupid as busy as a bee in Mystic Falls, let's hope our beloved characters take some time off from the supernatural to find their soulmates before it ends.

Check out more from The Vampire Diaries:

Which awkward love triangle moments in The Vampire Diaries had you embarrassingly looking away from your TV? Share them in the comments below.


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