Too bad he kept dying (and coming back to life). One time, Bonnie had to kill him to make a spell work. Thankfully, she remembered her CPR training.
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The masquerade was the moment when Bonnie started to see Jeremy as more than just Elena's little brother. Suddenly, he was "Hot Jeremy."
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Like that time he was an integral part of taking down Katherine at the masquerade. That was also an important moment because...
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No one really believed it possible but even before he became a hunter and took up the crossbow, Jeremy Gilbert had it in him to be a badass.
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Okay, Jeremy DID try to kill himself so that he could become a vampire to be with Anna forever only to discover (eventually) that his mission on Earth was very, very different.
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After Damon turned his stoner girlfriend into a vampire and Stefan had to kill her to save his life, Jeremy met another vampire who stole his heart. Can we really blame him for falling in love with Anna? No, no we cannot.
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Jeremy Gilbert is the smartass kid brother everyone secretly wishes they had. Even at his absolute worst, Elena still loves him.
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Jeremy Gilbert cried. A lot. A LOT. Maybe it was the pot. Maybe it was the fact that absolutely everyone he loved kept dying on him. We may never know.
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Vampire Diaries Quotes

He's your first love. I intend to be your last. However long it takes.

Klaus [to Caroline]

We met and we talked and it was epic. But the sun came up and reality set in.

Elena