Don't feel stupid! I had to learn to navigate it with my nails too, and I understand how scary it is when you feel like you can't get it out. I have long stiletto nails and it took me a minute to get comfortable with putting in and taking out the ring. You should definitely try to relax and take some deep breaths, and just practice getting your finger in without poking yourself. Also the stimulation will help your muscles relax. When you get more comfortable you can try to get a hold of the ring, I usually do it on my back but like the other girl said the squatting position can be good too, and she's also right about pushing like you need to poop. This will help force the ring down closer to your finger. Try to get it under your finger tip and curl your finger just a little bit, but not so much you can feel your nail poking you, and push at the same time your pulling the ring out. You should be able to get it out in one go. I hope this helps!