I personally find the pictures of the people with two(or more) colors of hair in a french/dutch braid or a bun look really cool and unique, so I'm just going to go ahead and say that I think you should grow it out and not cut it.. but that's just me
Maybe you could start doing henna glosses instead of a full henna treatment? It takes less time and maybe your regrowth will blend a little better with your hennaed hair? Obviously if you want to grow out your natural hair color you'd have to stop doing even that, but it might help with the transition a little bit
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