Tonight with your 13 to 17 year old
The prompt
“Does loneliness ever hit you even when you're around people? What does that feel like?”
What to listen for
If they can describe it, being physically present but feeling unseen, they're developing real emotional insight, and naming it is itself a sign they trust you enough to be honest about something uncomfortable.
If they say it doesn't happen to them, take that at face value for now, but leave the door open by not making this feel like a loaded question they need to have a dramatic answer for.
If real sadness comes through, resist jumping straight to solutions, let them know being around people who don't really see you is a real, valid kind of hard.
What this tells you
Whether and how they describe feeling lonely in a crowd shows you how deeply seen they currently feel in their everyday life.