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When we were walking in Italy, my pinky toe caught on a ridge in the pavement on a shoulder of a road and separated from my second toe, it felt sort of like it does when you hyperextend your pinky finger. It turned purple, swelled up, and was not happy to be straightened by my shoes (I only had 2 pairs of VFFs and my Keen cycling shoes). The swelling went down after a day or so, but the stiffness was pretty rough for at least that week (the entire bike trip, though I wore my Keens during the day). My chiro said I probably irritated the ligament and sprained the toe, and he knocked things back in place (boy did that feel good). After all that, it still feels a little stiff almost 2 weeks later.
The curse of free toes. Reminds me a lot of wearing gloves when you ski/snowboard (rather than mittens), which is how I know what it feels like to hyperextend a finger.