Uh-oh. There's that evil smile we've grown to both hate and to love on Damon.
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Caroline and Matt in "The Last Day."
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Jeremy looks on in the May 5, 2011 episode of The Vampire Diaries.
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Wait... what?!? Caroline reacts in surprise to Elena in this picture from "Resident Evil."
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Caroline and Stefan look as if they're about to find Elena in the wreckage after the wedding. Can anybody truly be ready for this moment?
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Lily is nothing but trouble, yet even so, there is something about this photo that a step beyond the norm, don't you think?
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What if Damon and Elena took the cure? Could Elena have a normal life again?
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This is the first of several photos that features Elena with a certain whimsical look on her face. Is she thinking back through her life?
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Vampire Diaries Quotes

Break out the popcorn, Blondie. Elena’s little sex romp isn’t over yet.

Enzo

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