So how does the Truest Believer become a downsizer?
1) VV is a mysterious condition, usually activating before the age of 10, but what is known, is there is some level of genetic basis to its presentation. This means when Henry Mills becomes the only VV in Storybrooke, he knows something is up.
2) If it wasn't that Varying Violets were, while a scientific abnormality, something that did happen in the outside world, Henry could probably use the fact he had it, to convince Emma magic was real. Yeah, shame that :P
3) Henry is cursed by Cora to shrink when scared or angry, hoping to use this as a way to get Regina onto her side, or at least control her through her soon-to-be tiny son.
4) While trying to break the sleeping curse her own way (not trusting Emma to get the cure from Malefficent) Regina uses a little of her remaining magic on Henry. Not only does it not wake him, but when he comes to, anger, fear and anxiety cause him to shrink
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