Tonight with your 5 to 8 year old
The prompt
“Was there ever a time you felt shy meeting someone new, what was that like?”
What to listen for
If they can describe the physical feeling of shyness (quiet voice, wanting to hide behind you, tummy feeling weird), that's great self-awareness, celebrate the noticing, not the shyness itself as a flaw. If they insist they're never shy, that's fine too; some kids genuinely warm up fast, and others just haven't connected the word "shy" to the feeling yet.
Listen for whether they describe wanting you close by during that moment, that's a completely normal, healthy sign that you're their secure home base while they figure out someone new.
If they say "I don't know," ask about the last time they met a new kid or grown-up and what that felt like right at the start.
What this tells you
How they describe shyness shows how much they currently rely on you as a safe home base while venturing into something new.