I am not the first person to observe that it sometimes takes several tries to plug in a USB connector (specifically the rectangular Type A connector, which is not reversible). There are memes about it, there are cartoons about it, and on sites like Quora, people have asked about it more than a few times.
But I might be the first to use Bayesian decision analysis to figure out the optimal strategy for plugging in a USB connector. Specifically, I have worked out how long you should try on the first side before flipping, how long you should try on the second side before flipping again, how long you should try on the third side, and so on.
For a high-level view of the analysis, see this article in Towards Data Science.