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I enchanted my gloves pink, but when I throw another chocolate bar in the well it says "No possible enchantment."Is it possible to enchant my leather gloves pink AND red?

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According to this,

They can be enchanted using Chocolate bars in the wishing well, you can enchant it to pink enchanted gloves or red enchanted gloves.

the key word being "or", so you cannot enchant a pair of gloves with both enchantments. However, you can get two pairs of gloves, one for each enchantment.

Note: The Merchant will start selling again the gloves after they are enchanted. It is possible to have both sets of enchanted gloves.

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No, but you can get two pairs of gloves and enchant them the two different colours.

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