Sydney moved around a lot, and was never able to get settled in one place. Given that the answer to a question is "a roaming soul", what is the question?
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Answer: How would you describe Sydney?

Tracy went on vacation and decided to rent a car. Given that the answer to a question is "needed transportation", what is the question?
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Answer: How would you describe Tracy?

Quinn conducted his business after hours at the shop so nobody would know. Given that the answer to a question is "guilty about his business", what is the question?
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Answer:
How would Quinn feel afterwards?