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Elena kissed Damon on his supposed deathbed, officially forgiving him from regularly breaking her heart.
Klaus refused them both as Damon had a werewolf bite and he wanted to recruit Stefan.
Stefan supported her choice to turn her back on Damon following this and kissed Stefan in front of him. Eventually, they returned to an unsteady friendship and after spending a day with Elena, Damon confessed to Andie that he wanted to be the bigger man for her, but also wanted to be himself.
He began an affair with Andie to take his mind off Elena.
Damon doubted her feelings for him when it was discovered she was sired to him so had to please him.
After Elena lost her humanity, she taunted Damon, threatening to go back to Stefan since the sire bond was gone.