Kendall was trying to explain something to Skylar secretly. Kendall gave Skylar a wink. Given that the answer to a question is "like things are in the clear", what is the question?
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Answer: How would Kendall feel afterwards?

Sydney spent time together with me while I was recuperating from an illness. Given that the answer to a question is "ask Sydney how I am", what is the question?
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Answer: What will Others want to do next?

Riley established close ties in the area before opening a business. Given that the answer to a question is "make money next", what is the question?
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Answer:
What will Riley want to do next?