Problem: Given the question: Aubrey succeeded at what they were trying to do and felt like a success. Given that the answer to a question is "keep doing well", what is the question?
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The answer is:
What will Aubrey want to do next?

Problem: Given the question: Jan and Bailey had a horrible first date, but Jan gave Bailey another shot. Given that the answer to a question is "enjoy the date", what is the question?
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The answer is:
What will happen to Jan?

Problem: Given the question: Carson didn't want anything to do with Bailey after Bailey wrongly accused them of cheating. Given that the answer to a question is "apologize to Carson", what is the question?
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The answer is:
What will Bailey want to do next?