Problem: Given the question: Casey was clueless with computers so Kendall made Casey's application to be helpful. Given that the answer to a question is "kind", what is the question?
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The answer is:
How would Kendall feel afterwards?

Problem: Given the question: Skylar had finally found something that he was better at than his brother, and Skylar challenged his brother to a soccer match. Given that the answer to a question is "proud of his accomplishment", what is the question?
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The answer is:
How would Skylar feel afterwards?

Problem: Given the question: Casey booked her trip to the Caribbean and started counting down the days until she left. Given that the answer to a question is "have a pet sitter come to take care of her animals", what is the question?
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The answer is:
What does Casey need to do before this?