There is also the fact how Henry would react to him–he may not really be that excited by the idea. He already has a shaky relationship with Regina as is, it might be difficult for him to get close Rumpelstiltskin with trust.
He does not fully trust Rumpelstiltskin–he warned Emma not to owe him anymore favors, and he always appeared uncomfortable around him. In recent episodes he seems alright in his prescence, but it might be hard for him to get close to him.
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