Curious

I think that it's because you like things acutely defined. When you encounter a situation you seem to have to understand a lot about the situation, by eg. proposing hypotheticals. Your overanalysis comes from this sort of need. The one thing I really think you need to do is trusting your raw emotions a bit more.

At a subconscious level, you likely understand a situation already, but to verify its truthiness as it were, you analyze it to bring it into your conscious mind. This manifests in things like hypotheticals, devil's advocation, and so forth so as to bring about an all-encompassing understanding.

What you need to realize is that you don't need this. That feeling you had initially is enough. Generally, you can just trust it. Sometimes there will be mistakes, and then you can ask for clarification and fill that little bit with the missing information.* When you come to have a good understanding of the human experience, your gut will be correct more often, and you can come to be more comfortable interacting with others, because you begin to understand what makes people feel one way, or what it is that can mark different forms of expression like sarcasm and irony vs. direct speech; and you can learn when each is appropriate.

*Here is a point where you're currently erring a lot. Over time, you've encountered a lot of situations with gaps. However, instead of asking, you've tried to fill in the gaps with your logical analysis. Many of the times, you've filled this in with incorrect assumptions that still make sense, and have solidified these in your mind as relateable fact when it isn't. After doing so, you've probably forgotten what you've even done this for. Now, when you communicate based on these wrong foundations, people get upset, judge you, etc.

So what it comes down to is feeling. When you read something (that's communication, rather than say a wiki article), the intention is to evoke a certain feeling. You can't treat these words like they're written law, picking apart their technical meanings to identify the legality of the sentence. Because in the end, the person who wrote it didn't do that, they simply wanted to get a point across, to share a feeling of theirs with you, and that is what you need to focus on reading.