Okay, so pretty self explanatory.
What is the most trouble you've ever been in in your entire life?
It can be trouble as in getting caught doing something by your parents or police...or trouble as in a terrible situation.
For me, the most trouble i've ever been in was when i got caught having a party when my parents were out of town. the cops got called because of noise and they called my parents...got grounded for like a month!!