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The first time they kiss in the books happens in 'The Struggle'.

In the Season 1 finale, Damon thought he kissed Elena but it turned out to be Katherine instead.

Damon kisses Elena on the forehead, if you'd like to count that in episode 8.

Also, Damon kissed Elena in the Return the first episode of season 2 he had just been rejected by Katherine she had just told him she never loved him and it was always Stefan. He came into Elena's bedroom it was basically a forced kiss.

Something that is important to know is in the Return the first episode of season 2 Damon says to Elena he kissed her and thought she kissed him back this was when Katherine was pretending to be Elena and Damon kissed her.

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12y ago
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12y ago

Damon and Elena kiss in the episodes "The New Deal" and "Heart of Darkness"

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Q: What season in the vampire diaries will Elena kiss Damon?
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