Depends on what it is that it gets stuck. Stick your finger in a closed tube like a marker cap or something and you have a vacuum seal that becomes difficult to break without letting air into the tube.
A kid getting their head stuck in between a railing is usually because of the shape of one’s head and ears. The ears fold back and compress easily going from the front of your face to the back, but going the other way they are unable to get out of the way.
Stick your hand or finger into an object like the top of a Clorox Wipe – the thing with those spikes to help tear the sheet. The “spikes” easily bend in the direction of the object inserted, but when the object is reversed, the spikes have no room to reverse direction so they dig into the object and don’t allow it to move. I think this was one of Jigsaw’s traps in a Saw movie.
It’s because of the skin and other tissue around the bone.
When you insert your finger into a tight hole, your finger skin&tissue gets pulled back behind the hole and the part that’s inside the hole has slightly less skin and tissue and thus your finger gets thinner when you’re penetrating a tight hole.
When pulling back, the skin&tissue gets pulled to the other side, making the part of your finger inside the hole have more skin and thus be thicker, the harder you pull, the thicker the part inside the hole gets.
To avoid that, you need to remove the friction between your skin and the hole by lubricating, and pull your skin back before pulling.
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