Casey's son had outgrown his baby clothes and no longer needed them. Given that the answer to a question is "needed to do some spring cleaning", what is the question?
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Answer: What does Casey need to do before this?

Skylar decided to be outspoken and gave their opinion freely. Given that the answer to a question is "defend their opinion", what is the question?
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Answer: What will Skylar want to do next?

Sydney used to be an ugly girl, but eventually turned out really well as if the ugly duckling. Given that the answer to a question is "a pretty girl", what is the question?
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Answer:
How would you describe Sydney?