Chocolate milk is *packed* with sugar. Regular milk isn’t.
When you dunk an Oreo in milk, you’re also dissolving the Oreo in milk. Because there’s no sugar in regular milk, the sugar in the Oreo dissolves pretty easily into the milk. Because there’s so much sugar added to chocolate milk, the sugar in the Oreo doesn’t dissolve into it as easily because liquids can only dissolve so much sugar before the sugar stops dissolving. Chocolate milk is a lot closer to the point where no more sugar can dissolve than regular milk is, so it doesn’t penetrate the Oreo as easily.
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