Jeremy got a job waiting tables at the Mystic Grill which was kind of weird since Matt Donovan had been working there for years at that point and was still only a busboy. Must have been Jer's biceps.
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Theirs was a love story for the ages, unfettered by death, space, time, or any other mystical creature which threatened to separate them. Except ghosts. They didn't really fare so well when Anna started showing up again.
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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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Vampire Diaries Quotes

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

Damon: You know what they are? Children. Like lighting a candle's going to make everything OK, or even saying a prayer. Or pretending Elena's not going to end up just like the rest of us murdering vampires. Stupid, delusional, exasperating little children. And I know what you're going to say: 'It makes them feel better, Damon.' So what? For how long? A minute, a day? What difference does it make? Because in the end, when you lose somebody, every candle, every prayer is not going to make up for the fact that the only thing you have left is hole in your life where that somebody that you cared about used to be. And a rock with a birthday carved into it that I'm pretty sure is wrong. So thanks, friend. Thanks for leaving me here to babysit. Because I should be long gone by now. I didn't get the girl, remember? I'm just stuck here fighting my brother and taking care of the kids. You owe me big.
Alaric: I miss you too, buddy.