In between vampire killing and girlfriend kissing, Jeremy made sure to brush his teeth. We're sure Mama Gilbert is proud of her baby boy and his commitment to personal hygiene.
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In his spare time, Jeremy Gilbert took up the crossbow to hunt vampires. He's the only other person we know who is able to give Daryl Dixon a run for his money.
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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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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

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

Dear Elena, yes you heard that correctly. Hell has frozen over. I'm writing it all down. Granted, I'm half a bottle in thanks to my 1950 Chateau Cheval Blanc, a bottle I waited 65 years to open. I used to spend nights sitting in my wine cellar convincing myself I could hear it age, tannins growing, fermenting, but appreciating its beauty didn't make time go by any faster. The bottle just laid there on its shelf, torturing me while I waited for Katherine and time stood still. Eventually I convinced myself that no sip of that wine could ever taste as good as I dreamt it would. And that is the story of why I drink bourbon. I don't know who I am without you, but I know that as long as I'm with you, time will stand still. So who is Damon Salvatore without Elena Gilbert? A selfish friend, a jealous brother, a horrible son? Or maybe with a little luck, I'll do right by you. Because you may be a thousand miles away or a hundred years away, but you're still here with me and my heart is right there in that coffin with you. Until you come back to me.

Damon