Tonight with your 13 to 17 year old
The prompt
“What's something embarrassing from a while back that you can actually laugh about now?”
What to listen for
If they tell the story easily and laugh while doing it, it means they've made peace with an old version of themselves and don't need to protect that memory from you, they feel safe enough to be seen mid-blooper.
If they tell it but wince or downplay it, they might still be a little tender about it; that's worth just noting gently, not digging into.
A flat "I don't know, nothing" usually just means they don't want to hand you ammunition tonight, not that nothing ever happened, let it go and it'll come up another time.
What this tells you
The ease or discomfort in how they tell this story shows how far they've come in accepting themselves, flaws included.