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

Elena: Why don't you ever let anyone see the good in you?
Damon: When people see good they expect good. And I don't wanna live up to anyone's expectations.

You want a love that consumes you. You want passion and adventure, and even a little danger... I want you to get everything you're looking for. But for right now, I want you to forget that this happened. Can't have people knowing I'm in town yet. Goodnight, Elena.

Damon