[Cavernio]

I can make fun something a friend did such that we both laugh about it. There are some people, however, with whom I can't do that with, even friends. What's the difference between these situations? I have a very hard time describing it. The difference between when I can do that and when I can't do that is very similar to when bragging or otherwise saying arrogant things is going to be acceptable. I can't pinpoint the specifics of it easily, but it's quite few situations, IMO, where this can happen.

To be humble about something and then have someone praise you for something is a lot more meaningful, because they think of it completely on their own. In that sense it's much more selfish to be humble. Yet it still works out better for both you and for the other person.

Arrogance is not taboo in some cultures because arrogance is largely culturally defined. To describe how arrogance is different from one culture to another where the same actions come across completely differently is not really describing how arrogance, itself, is different.

Arrogance is not something defined easily. I see it as a general coming across as 'I am better than you' in mannerisms, whether they are better or not. But even with that description, there are many people who, when someone else calls them arrogant, I'd have to agree, but their actions don't bother me in the least. Probably because I don't interact with them such that I care about what they think enough for me to label them with something negative.
The certain subset of people that can get under my skin the most are intelligent, arrogant people who perceive differences between how I, or others, are from them as a difference in intelligence rather than a difference of perspective. This is infuriating because those people come off as closed-minded. Like, nothing I say or do will actually affect their own opinions because they perceive that their view is the best view to have.
Someone who is arrogant comes off to me as they are closed-minded as well. I think necessarily being more closed-minded is part of the definition of it, actually, thinking about it more. Like, because they think so highly of themselves, true or not, they will weigh their own opinions and ideas as above someone else's just because they are their own. Then if this is someone who is good at debating or is generally intelligent will then be able to back up their perspectives well, even though there's often plenty of cracks in their perspective.

Like, pretend you're arguing with someone who's stupid but arrogant. It quickly becomes obvious that you cannot get through to them about a given topic because they perceive that they just know better. Now make that same person smart, and when you find a hole in something they've said, they are quickly able to weave around it and argue against it. They will change their perspective to actively defend their position in such a way that in order to get them to see that they have this error, you have to refute all of these other, only loosely connected problems. And then, if you CAN'T break down their arguing for whatever reason, it just reinforces their perception of their intelligence, and also their perception of their not-quite-right opinion, when the reality is that they're just fucking stubborn but are smart about it. Like, people like that are the types who can actually think that genocide is alright and then can also make it happen.

I value open-mindedness a lot, and ability to see things from someone else's perspective as very important. Because perspective, even though there are more true and false perspectives one can have of some aspects of the world, they are all ultimately false, inaccurate, poor representations of truth.

And then there's the fact that in order to be better than someone else, you are basically going to be insulting them because that's dichotomy for you. That's another reason why humbleness exists. People don't like being told they are not good at something.

I'd suspect in cultures where people go around bragging and that is expected, it's probably a sign a weakness to not be bragging. It also might play a more important role in that person's actual safety, since I think (and I could be wrong here) cultures where that common practice, there's little effective policing and such. Think of being in a gang. The moment anyone sniffs weakness, you're dead. In our shared culture though, you are not weak if you do not brag.

As to the final point, is being humble an inaccurate representation of oneself, that depends. If you're sitting there trying to hold your tongue and not brag, then yes. If you are naturally inclined to not say anything about yourself, then no. This ties into personality more than an anything else though.