Bailey yielded Sydney's income because she just won the giant lottery that day. Given that the answer to a question is "make sure Sydney got their winnings", what is the question?
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Answer: What will Sydney want to do next?

Kai learned to play guitar by teaching themselves using the Internet. Given that the answer to a question is "accomplished and able to do anything", what is the question?
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Answer: How would Kai feel afterwards?

Ash was so beautiful they took Jordan's breath away. Jordan immediately asked Ash to marry them when they first met. Given that the answer to a question is "flattered", what is the question?
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Answer:
How would Ash feel afterwards?