Question: Sasha was Skylar's prom date and Sasha broke it off. Given that the answer to a question is "get a new date", what is the question?
Answer: What will Skylar want to do next?

Question: Kendall needed to get onto the roof, so they got a ladder. Given that the answer to a question is "Successful", what is the question?
Answer: How would Kendall feel afterwards?

Question: Robin made the worst cake ever for the upcoming social gathering. Given that the answer to a question is "buy a cake", what is the question?
Answer:
What will Robin want to do next?