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Most of the time when I wear my hair in a ponytail, it feels as if the hairs rooted at the crown of my head are being pulled... and I mean to the point where it hurts so much I have to take off the ponytail tie. I've tried wearing the tail loose, and that works some of the time. I've also tried those really small terry-cloth ties so that I can just pull my hair through it without having to wrap the tie 2 or more times. The small ties don't pull on my hair, but they don't hold the ponytail all that well either. Maybe I just have weak and/or sensitive roots. Any ideas or suggestions? Perhaps someone can recommend a tie that wont cause the hair to get "pulled."
Is it long enough to braid, either as a ponytail or as pigtails?
How long is your hair, and how long have you been letting it grow? Once you can get the shorter front hair to the point where it can be tied in back, you won't have to pull it so tight. I can't wait for the day when I can wear a really loose ponytail and keep my ugly ears covered!
Try a braid. It doesn't need to be a full braid. Braiding even only 2 or 3 "stitches" before applying the ponytail holder will make a big difference. This allows the stress to be applied evenly over all the hairs instead of primarily the perimeter, in the case of a standard pony tail.
If you don't want to braid, here is something I do. First brush your hair as evenly as possible. What you are trying to do is apply pressure as equally as possible, so an even brushing really helps. Next, apply the pony tail holder a slight distance away from the scalp and when finished, grab two portions of hair from the inside of the holder and spread apart in a way that scoots the holder up. This technique helps to transfer some of the pull from the perimeter to the interior of the pony tail. It won't last long if the holder is too loose.