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Mine does... And it really doesn't matter how tight it is. My hair is quite thick, so if it grows much past my shoulders it will hurt when pulled back by the end of the day. When that starts happening, I know its time for a trim.
 
I don't do ponytails (face is too fat and round), but I use headbands and am always forgetting my sunglasses on top my head. Today I got a headache from the pollen and having the glasses on my head. When I took them off, my head felt better! ::)
 
Did you ever bend your hair the wrong way? That hurts. My hair used to be passed my knees. I cut it to my bra strap, but I'm letting it grow out again. Don't really know why. I guess I just like long hair. Everytime I see someone with long hair I like it, but then all I do is wear it in a ponytail or a bun. Then I see a really nice shorter style and want that too. I have nice hair, not too thick, but not thin either.

PS: I donated my hair to locks of love!
 
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