Amara is the progenitor of the Petrova line and the woman who looks like Elena and Katherine, Damon's lovers. They met each other during Silas' plan to destroy The Other Side and during their short time together, they were friendly.
In Death and the Maiden, Damon introduces Stefan to Amara while they watch her as she suffers with the effects of being the Anchor to The Other Side. He stops her from committing suicide (she had bitten her wrists in an attempt to make herself bleed to death). Damon later finds Amara after Silas takes her from the Anchor transferring spell Qetsiyah was performing. He tries to feed her his blood, but it won't work. He pleads with her to stay awake, but Amara tells him to let her die. She then passes away with Damon next to her.
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"I would write... Dear Diary"
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Damon dated two of Amara's descendants/doppelgängers, Elena and Katherine.
During the time in which they knew each other, Damon gave Amara several nicknames, including Crazy Pants.