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TV Guide has some scoop about Damon and what is to come for this seemingly lonely character.
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"Will Damon ever be happy on The Vampire Diaries? — Sarah Jane

MICKEY: It's unlikely, Sarah Jane. But look for a sun-kissed beauty to lighten his mood. She won't flinch when Damon attempts to sabotage their flirtation with his acidic charm, but that's because her interest in him is not personal. Said beauty has come to town to investigate Mason Lockwood's disappearance, and this lady does not have a thing for bad guys."

Source: TV Guide Megabuzz