Alex put Tracy to bed after the party where Tracy drank way too much. Given that the answer to a question is "were worried that their friend would be ill", what is the question?
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Answer: How would Alex feel afterwards?

Sydney turned heads when they attended class wearing their new designer jacket. Given that the answer to a question is "proud of their purchase", what is the question?
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Answer: How would Sydney feel afterwards?

Casey spent a lot of money on a car and liked it a lot. Given that the answer to a question is "drive their car", what is the question?
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Answer:
What will happen to Jan?