The song says, "Take a sad song and make it better..." Have you
ever had to do this, have
you ever had to make the best of a bad situation? Tell me about it.
(click here to listen to Ms. Ruhl's story)
(click here to listen to Mr. Collins' story)
Did you ever play it cool (= 冷静を気取る)? Tell me about it. What was the situation?
did you want to "show how cool" you were? How did it turn out?