Is the fact that the standard USB connection (rectangle) is not really 180 degrees symmetric (despite a shape that indicates it should be), usually takes 3+ attempts to get it in. Damn it, Jim, a spin-1/2 connector!
Protip: The USB emblem goes "up". The logo is trademarked, and without it the cables are too frustrating to use. An interesting feat of human engineering indeed.
Now, let us travel through time far enough into the future that we come to appreciate the greatest connector design possible:
First, consider the connector with zero lines of symmetry, such as USB, or a polarized pronged plug. There is a 2D plane that the connector travels orthogonal to and which it must breech in order to complete a connection docking sequence. Consider this plane slicing through your connector and receptacle's contacts. Note that there is one receptacle surface for one connector pin passing through the docking plane.
To the Future! Copy and rotate your receptor 180 degrees in place along the docking plane. Eliminate any conflicting isolation surfaces, and move the pins such that they do not interact with each the other's connection surfaces. Now you have a reversible connector with one line of symmetry in the receptacle. The connector pins can occupy both sets of receptacle contact surfaces, but need only occupy one position to complete the electrical circuits.
Advance! Now we will perform the same step again, but with a 90 degree increment. Behold! A square connector!
60 degrees? Hexagonal connectors! Note that just imagining it we can nearly taste the hex filled future!
Onward, to 45 degrees, and to victory! Octagonal connections even mirror our futurist desire to slice the corners from our square UI windows, and tabs.
Oh integration, you foul beast. Clearly to see furthest into the future we must have infinite lines of symmetry in our docking plane -- BUT HOW?! With all pins occupying all positions across the USB connector, the left side interacts with the right side. Since connector pins need only exist in one position we need only make the connector pins have zero lines of symmetry -- move all the connector pins to one side. Simultaneously we have a perfectly round receptacle -- Ah, but all intersecting isolation surfaces are removed, this leaves us with only a flat ring of contacts and several pins.
So, now we will enter a new Dimension! We can stretch the docking plane in the 3rd dimension along the orthogonal connection axis! BEHOLD! We have discovered the most futuristic connector of all time! The Head Phone Jack!
Now, what's old can finally be new again. Story time is over, now get off my lawn.