Assateague is a large island off the coast of Virginia; it is inhabited by wild ponies.
"can you dig it" is also the same thing as "can you roll with it" or "do you find it acceptable". basically, meaning if one can agree with a certain thing.
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According to TeacherVision, analogies can be used to introduce new vocabulary or compare situations or characters in literature. Research shows connecting what children already know to new concepts and ideas sharpens their focus and deepens their understanding.
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