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Does ichigo ever kiss orihime?

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No but she came very close to kissing him before she left for Hueco Mundo, even though he was asleep. Ichigo has never expressed any romantic interest in Orihime (or any other character).

When in Ichigo's body, Kon kissed Orihime's hand when he was free. However, this is Kon in Ichigo's body, not Ichigo.

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