Problem: Given the question: Jesse took a long look at his girlfriend Robin and put his head down sadly. Given that the answer to a question is "Try to cheer up Jesse", what is the question?
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The answer is:
What will Robin want to do next?

Problem: Given the question: Carson brought Casey inside even though he was having fun playing with the neighbor's dog. Given that the answer to a question is "upset in not being able to play longer", what is the question?
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The answer is:
How would Casey feel as a result?

Problem: Given the question: Casey was proud to see Bailey get perfect grades and urged the shy Bailey to accept an award. Given that the answer to a question is "get Bailey out of their comfort zone", what is the question?
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The answer is:
What does Casey need to do before this?