Question: Ash and Jordan had been lovers for several years. Given that the answer to a question is "appreciative", what is the question?
Answer: How would Ash feel afterwards?

Question: Jesse married their high school sweetheart last summer. Jesse lived happily ever after. Given that the answer to a question is "have a first date", what is the question?
Answer: What does Jesse need to do before this?

Question: Skylar worked so hard that week that she had to take a break and spend the next week relaxing. Given that the answer to a question is "finally relax", what is the question?
Answer:
Why did Skylar do this?