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Well you're already documenting and communicating....
Is there any way to bring in the department chair next time you have a sit-down meeting with the parent? I feel like administratively, the DC is your peer and you might need an extra pair of eyes on this situation in case it ever escalates.
Does your school have a "Student Support Team?" In the DC schools that is a committee of teachers and other professionals who might be able to look at a situation closely.
Child welfare/social services?
I feel for you, I really do. One of many reasons why I left teaching/education.
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