The first try, you were partially miss-aligned and just gave up too early, making the assumption that you had the plug upside down.

Second try, you are actually upside down, so even with additional effort you can't plug it in.

Finally, you now know it was upside down the previous attempt (you probably looked and verified), so you try a third time with renewed determination and assurance until it actually works.

Moral: Don't give up on yourself so soon. Your instincts and intuition can guide you in the right direction more often than you think.

Sometimes the alignment has to be very precise to get it in, and when it isn’t, it causes you to think you’ve used the wrong side/angle - especially when you aren’t looking at it directly.

The Heisenberg uncertainty principle. Both sides are the right side until you try to plug it in, at which point the wave collapses to reveal the reality.

Sometimes, it's just a matter of how much force you apply. On the first try, I push gently because I don't want to break something due to getting the orientation wrong. On the second attempt, I'd have verified the correct orientation through other means and will push more confidently.

Others have covered why the human response is to try the other way and then be surprised at the original direction. The core problem is the initial USB design. It should have been made either to accept both ways (like it was eventually with USB-C) or made obvious what side is what with an asymmetric shape or a required marking. Some manufacturers actually do put some type of indication on their USB plugs, but it could be either side.

Schrödinger's USB.

Inside the connector is a tiny cat that always lands on its feet, strapped to a piece of buttered toast. The whole thing causes a paradox and now I’m my own grandpa.

I blame whatever this is.

USB type A plugs are spin-1/2 particles. They have to rotate 360 degrees, not 180, to be flipped over.

https://en.m.wikipedia.org/wiki/Spin-1/2

My friend David refused to believe he was plugging USB cords in the wrong way. There were always two or three completely mangled USB ports on his computers.