Stefan and Katherine have one of the most complex romances in The Vampire DiariesThe line between love and hate grows blurrier with each season that passes, and circumstances cause Stefan to question the content of Katherine's character. Depending on the nature of the threat looming above Mystic Falls, the two find themselves on the same side as often as they do the opposite.

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Stefan and Katherine's love story spans decades, and while it originates in 1864, new information about their romance continues to come to light. It can be difficult to keep track of the years, but Katherine and Stefan's relationship can be summed up through a handful of crucial moments.

Stefan And Katherine Fall In Love

Stefan and Katherine meet in The Vampire Diaries.

Although the pilot begins during the 21st century, there are several great flashback episodes of The Vampire Diaries that help fill in the gaps. Stefan catches Katherine's eye the minute she sees him and an immediate connection is formed.

In the present day, Stefan refuses to believe that anything he felt for Katherine was real, but his argument doesn't hold up well. The two fall in love before Katherine reveals her vampirism and compels Stefan's fear away. While what she does to him in 1864 is wrong, it's clear that Stefan's love isn't due to mind control.

Katherine Checks Up On Stefan Through The Decades

Katherine checks up on Stefan in The Vampire Diaries.

Stefan might not have wanted to be a vampire, but Katherine makes the choice for him. Although the two have no face-to-face interaction for decades, Katherine never abandons Stefan as he believes.

It isn't revealed until later on, but Katherine checks up on him during the years after she fakes her death. Because she's on the run from Klaus, every move Katherine makes is thought out and premeditated. Yet, she continuously puts her life at risk to ensure Stefan's well-being.

Stefan And Katherine Reunite

Stefan and Katherine up close in The Vampire Diaries.

While Katherine watches over Stefan throughout the decades, Stefan spends the majority of his immortal life believing Katherine is dead. His love has morphed to hate and he blames her for everything that's happened to him and his brother.

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They don't have the romantic reunion Katherine's hoping for, and she's immediately upset by his relationship with Elena. Katherine spends over a century waiting to reunite with Stefan, so it's understandable that she's put off when he falls in love with her doppelganger. Still, Katherine has a lot to atone for, and Stefan can only see her as the enemy.

Katherine Saves Stefan's Humanity

Katherine gets through to Stefan in The Vampire Diaries.

Saving Stefan's humanity is one of Katherine's most meaningful romantic gestures in The Vampire DiariesIt's rare for Katherine to choose someone over herself, but Stefan is an exception to the rule. By warning Stefan about Damon's impending doom, she protects both Salvatores and prioritizes their lives over her freedom.

Everything Katherine does in the series relates back to Klaus, as she spends five hundred years on the run from the man who slaughtered her family. Yet, when she finally has the chance to kill Klaus for good, she doesn't take it for Stefan's sake.

Stefan Stops Katherine From Killing Herself

Stefan saves Katherine in The Vampire Diaries.

In season 2 of The Vampire Diaries, killing Katherine is Stefan's priority. He's willing to do whatever it takes to get rid of her in order to keep Elena safe. A lot changes over the seasons and it's clear that Stefan still has an emotional attachment to Katherine, regardless of how often he denies it.

She gradually begins to show a more human side to herself, prompting Stefan to save her life when she jumps from the clock tower. The roles are finally reversed, and while Katherine would rather die quickly than succumb to old age, Stefan isn't fond of either option.

Katherine Earns Back Stefan's Affection

Stefan and Katherine kiss in The Vampire Diaries.

The series has a knack for hate-to-love relationships, and Stefan and Katherine are just one example. They go from lovers to enemies to lovers again, when Katherine becomes human and begins to show a more empathetic side of herself.

Stefan's feelings appear genuine for the first time since 1864, and there's a brief period when it seems Katherine could truly be worthy of Stefan's forgiveness. Unfortunately, her impending death doesn't give their relationship the time it needs to properly evolve.

Stefan Changes Katherine's Worst Memory

Stefan changes Katherine's worst memory in The Vampire Diaries.

Other than Nadia, Stefan is the only person who shows Katherine compassion during her final hours. Klaus and Rebekah even travel from New Orleans to celebrate her death, while Damon organizes a Katherine-inspired drinking game on the floor below.

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It's understandable why everyone's anxious to be rid of her, but Stefan understands that Katherine's sense of self-preservation comes from her traumatic experiences. After her baby is taken from her arms and her family is slaughtered in cold blood, Katherine is forced to adapt to survive. Stefan replaces her bad memories of the night with good ones and absolves her of her guilt.

Katherine Pretends To Be Elena And Pursues Stefan

Katherine pretends to be Elena and dances with Stefan in The Vampire Diaries.

If Katherine had accepted her fate and died of old age, she likely would've held a special place in Stefan's heart. Yet, she does whatever she can to survive, no matter the cost to others. Katherine's intentions are a bit confusing, as she intends to win over Stefan while posing as Elena.

From day one, Katherine has been certain that Stefan's love for her is real, so it's questionable why she would want to pursue a fake relationship with him. However, it becomes apparent that Katherine is desperate for Stefan's love in any capacity.

Katherine Confesses Her Love For Stefan Before She Dies

Katherine confesses her love to Stefan before she dies in The Vampire Diaries.

Up until the moment she dies, Katherine never stops believing that Stefan is her soulmate in The Vampire Diaries. Stefan doesn't see things the same way, but his determination to find the good in her throws things into question. While Damon develops a hatred for Katherine, Stefan is never able to mirror his brother's feelings.

Stefan's morals come above all else, and Katherine's final actions leave him with no choice other than to let her go. She confesses her love before Stefan expels her from Elena's body, and he is visibly upset by the action. If Katherine had done just a few things differently, there's no saying where she and Stefan would've ended up.

Stefan Kills Katherine And Himself

Stefan holding Katherine in the Vampire Diaries finale

Stefan and Katherine do go out together, but it's not under very romantic terms. The characters use Stefan and Caroline's wedding to lure Katherine to Mystic Falls, and she makes a grand return from hell. Even after sealing her fate in The Vampire Diaries Season 5, Stefan still has a hold on Katherine's heart.

Sadly, her love for him isn't enough to stop Katherine from enacting her evil plan, and Stefan kills them both to save the town. Their love story comes to a tragic end, as while Stefan finds peace, Katherine's fate is left unknown.

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