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Henry did attempt to engage with Rumple a bit in 2x15, but since Rumple was quite dismissive then (due to the prophecy, but Henry didn't know that) I think Rumple would have to be the one to initiate now.
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Agreed. During the whole Pan thing though when they were back in SB Rumple seemed to be friendlier and better towards Henry. Explaining how the magic, and the bracelet would work so he wouldn't have to worry. And apologizing for not trusting that it was him and not Pan.