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In the series, yes, she has sex with Caleb.. then she finds out that Caleb was spying on her for Jenna. But she doesn't listen when Caleb tells her that he didn't actually tell Jenna anything because he liked Hanna too much (loved her actually) and he didn't think that Hanna was who Jenna thought she was.

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Q: Did Hanna lose her virginity in Pretty Little Liars?
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