Jan worked hard to overcome her fear of flying and eventually took a plane to vegas. Given that the answer to a question is "face her fear and overcome it", what is the question?
Ans: Why did Jan do this?

Kendall got milk for all their friends so they could have it with their snacks. Given that the answer to a question is "enjoy the milk", what is the question?
Ans: What will Kendall want to do next?

Robin told my parents he would want to marry me some day. Given that the answer to a question is "proud of himself", what is the question?
Ans: How would Robin feel afterwards?

After a long day of playing together, Kendall challenged their friend to a contest. Given that the answer to a question is "wanted to see who would win", what is the question?
Ans: Why did Kendall do this?