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My 4 year old is very shy around strangers but a chatterbox when she's around family. The problem is, when you ask her a question, most of the time her response is "I don't know" After school I pick her up and ask how her day went and she answers "I don't know." I ask what she did at school and she says "I don't know." I try asking her simpler questions like "Did you play outside? Did you color?" and she can answer yes or no, but never explains what she did.
Shyer children generally have a harder time warming up to strangers and can be anxious in new situations. So you first technique is to help her practice the first thing she'll do when she gets to a new place. Be matter of fact: "We're going to Jenny's house. Sally will be there, too. When we go inside we'll meet the mom and you and I will say hi! Now let's practice." You literally role play the scene before you go or meet someone new. She can practice with puppets, her dolls, or teach the dog, but shyer children benefit from practice and knowing what to do. As for when you pick her up from school, you may want to wait just a bit. The pick up and drop off times are usually the most stressful for a shyer child and she needs to decompress. Once home, you now turn the next ten minutes into a relaxed "chat." It might help her to draw what she did - or even play it out with little figures. Shyer children open up more if you sit side by side (not face to face) and allow them to do something (or hold something) while they speak. Somehow it gives them security. Also try making the "talking" into a "telling game" - instead of telling you, she tells someone else. Try taking turns (you go first, then it's her turn, then it's you turn). The trick is to gently get her to open up using questions that require more than yes or no answers. It may also help if she shows you (from her folder or the teacher's worksheet) what she did and describes the activity instead of relying only verbally.
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