My daughter used to be very much a highly sensitive child. She was the baby to cry at playgroups if I so much as stretched away from her to toss something in the trash. She would take pretty much the entire duration of playgroup to warm up enough to actually play and even then it was generally only if I was right by her side. We never really even tried having sitters nor did we ever try preschool. We tried taking her to this free circus thing at the library once and it was horrible. She screamed like you would not believe and just wouldn't calm down so we had to leave (there were clowns on stilts... and anoither one we brought her to had a guy on a unicycle which caused the same reaction). Oh, and at stores she would freak out if someone spoke to her which always made check-out hard.
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However, at some point she transitioned to being just a little bit quiet when she isn't totally comfortable. She is the kid in gymnastics who will stand back and let other kids cut in front of her, BUT other than that, she seems like she isn't at all sensitive anymore. Part of what may have helped is she has a very close friend and she'll go off and do stuff with her. She's also homeschooled, but in lots of activities. She now is very social and will easily run off with kids... I actually find myself missing the sensitivity because she used to observe and analyze before acting, now she just acts and I get so frustrated with some of the things that happened in the name of "I was PLAYING, that's why I overfed the fish and cut off my hair". And at the moment she is out with my parents after a sleepover... I actually sort of miss the days when she actually needed me. Recently she's acting like a teenager, like she'd rather be out with friends all day and having nothing to do with me!
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I have no idea how this transition happened, but I'm wondering if it's at all related to the fact that she's pulling away in her own time. Other than the hour class here a few times a week, she isn't away from us much. She started with her independent (without parents) classes at age 3, but even that was dance class at the studio I worked at and we were right outside the window. Funny how she actually did better once she started without us, though. I remember they would dump toys in the center of the room and tell each kid to pick one and dd wouldn't do it unless she was firmly attachet to my finger and I was right with her. It's crazy how far she has come since then. And for the record, she is 5 now. But I'd definitely say having lots of friends to run off with has probably helped. Good luck! I know exactly what it's like!