With a head getting stuck in a fence it’s more about a specific head position being achieved that allowed passage in but once that’s done their head position changes and it’s more difficult to get out. They must achieve the same head position to achieve freedom.
As for rings I’m less certain. Perhaps it’s because of the shapes of the fingerbones? They allow easier sliding off than on.
It is “way harder” only if the shape of the “thing” in question is irregular (think of an umbrella stuck through a mesh of sorts). Putting a needle into a cucumber is not easier than pulling it out, yet a sawtooth stinger (like a bee’s, or other bugs) will catch on while being pulled out and make it harder.
Okay, so take an arrow for example here… And bear with me but this will make sense in a minute. The shape allows for the arrow (diamond shaped or triangular) to puncture flesh, but the pressure from the body closes around the arrowhead and makes it very bad to pull out, causing more damage as it goes in.
Now, you want to think about the shape of the head and realised that your ears make a similar shape as an arrow. You can go forward, but not back as your ears aren’t shaped that way. You put your head through the bars, you might not get it out.
Knuckles have a similar effect with their shape, and skin basically smoothes out to allow the ring to pass the knuckle bone, then somewhat rolls up against the knuckle to stop the ring going back.
Have you ever seen these [screws](https://www.amazon.ca/10x50mm-Screw-Plastic-Anchor-Expansion/dp/B07N8GGX3D)?
Notice how you can compress the fins when you push it into the wall? but then getting it out results in the fin getting jammed?
Same with head or ring. When you put it in, you relax, twist, turn, and allow the object to slide through. to remove it as easily, you need to replicate the process…. in reverse. Which, unfortunately, due to the fleshy nature of our brain, we cannot replicate the exact process. which often leads to panic or brute force. which means we will likely spend much more effort in getting it out.
And also if it was easy, the human population would be in rapid decline.
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