Ouch my big toenail!

[KnottedYet]

Sometimes if I don't keep up with my toes and the nails get just a smidge too long the pressure from the shoes will make my nail hurt like you describe. Sometimes it even acts like the edges of the nail bed are very irritated (they'll even get red and a little puffy)

I trim the nail and file it smooth and wear sandals for a couple days, which fixes it just fine.

Is your big toe longer than the toe next to it? (i guess that'd be the pointer toe). I had a shoe guy explain to me that I had size 9.5 big toe, but size 9 other toes; and he told me to buy size 9.5 shoes so my big toe would have the room it was meant to have. That also helped with the nail thing.