Damon looks lost in thought here, doesn't he? The vampire does have a lot going on in his life.
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We'll drink to this flashback! Lexie, Stefan and Damon are in the 1940s on "We'll Always Have Bourbon Street."
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What do you think of the Salvatores in uniform? We're in the 1940s with the brothers in this scene.
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We're back with Lexie and back to the 1940s in this Vampire Diaries photo. It's courtesy of the episode "We'll Always Have Bourbon Street."
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Yes, ladies, it's Damon Salvatore in uniform. This is a photo from "We'll Always Have Bourbon Street."
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We flash back to the 1940s on the 12/6/12 episode of The Vampire Diaries. Do you like Damon in uniform?
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Ready to shriek, Delena lovers? Damon and Elena share a slow dance in this shot from "My Brother's Keeper."
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Ready for the Miss Mystic Falls Pageant? This photo of Damon in a suit ought to help, right?
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Why is Damon all dressed up? For the Miss Mystic Falls Pageant, of course. He looks good, huh?
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Damon is back in school in this photo. He's in the classroom of Professor Shane.
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Bonnie and Damon have some questions. Will Professor Shane have the answers?
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Damon and Elena square off in this scene from "We All Go a Little Mad Sometimes." The former suffers from some hallucinations throughout the episode.
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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