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Currently you are able to watch "My Dress-Up Darling - Season 1" streaming on Crunchyroll Amazon Channel or buy it as download on Apple TV, Microsoft Store.
There are no options to watch My Dress-Up Darling for free online today in Canada. You can select 'Free' and hit the notification bell to be notified when season is available to watch for free on streaming services and TV.
Wakana Gojo is a high school boy who wants to become a kashirashi--a master craftsman who makes traditional Japanese Hina dolls. Though he's gung-ho about the craft, he knows nothing about the latest trends, and has a hard time fitting in with his class. The popular kids--especially one girl, Marin Kitagawa--seem like they live in a completely different world. That all changes one day, when she shares an unexpected secret with him, and their completely different worlds collide.