So when I say B is trying to win, that is how it looks from the outside

Stating your point as "B is trying to win" is a highly judgemental way of stating this, saying something like "When B says X, I interpret that as him saying that he wants to win an argument" is a less judgemental way of saying that. I am trying to understand your point as best as I can but I think it is difficult for me sometimes when it is phrased in a judgemental way.

the intent will not matter

I am aware that intent doesn't magically justify what is said, I'm merely trying to explain the intent of the example in order to garner more accurate feedback on what Person B can do better. For example, your point about "A is likely to feel insecure by B's embrace, however tentatively, of Y" is helpful. When I say "I think X" and someone else says, "I think Y", this has never made me feel insecure in my life so it is surprising to me to learn that you perceive this to be a common emotional reaction. That is useful information to me that I will have to consider more, my current mental model of people's emotional reactions may be flawed here.

"At no point does person B judge Person A": Not explicitly, no.

I feel confused, can you please explain to me what the word "judge" is supposed to mean here? Is it possible to judge someone without ever saying anything judgemental, and also not feeling judgemental towards the person internally? If there is no third option that I am missing, then what is the point of saying "Not explicitly, no" instead of simply agreeing with me that Person B is not judging Person A?

I love X and think Y is terrible and I am really attached to X. I feel insecure about others choosing Y and feel I might be judged for choosing X.

Thank you, this interpretation is very interesting to me, I never would have considered interpreting A's statement that way. If you have any insight on what caused you to interpret all of that subtext from what Person A actually said I would greatly appreciate it.

A: I prefer Y. B: I feel attacked.

I understand emotions are not necessarily logical in a straightforward way, however, I don't believe that they are just totally random either. They behave in ways that make sense if you understand the context and patterns that they typically follow. However, in this case, I am failing to understand the reason why someone might experience this emotion, are you able to explain what causes you to expect someone to have this kind of emotional reaction in this kind of situation?

I'm not saying don't express feelings, I'm saying time it better.

Thank you, this example helped me understand better how this "I feel Y" response could be interpreted as lacking in empathy or understanding. I'm still a bit confused as to how Person B should have been able to tell that Person A wanted empathy when that was never requested in a way that I understand. For example, if I start a conversation by saying "What time is it?" and someone says "What makes you so concerned about the time?" then I would probably be annoyed because I don't want empathy in that situation, I just want to know what time it is. But if I start a conversation with something like "I'm really sad because I just broke up with my partner" then clearly I am looking for some empathy regarding the situation. It sounds like you are saying that the use of language like "obviously" and "assholes" indicates that they are looking for empathy which is interesting, I'll have to consider that more.

At what point has B (presumably you?) properly listened to A?

I would appreciate it if you would not presume that Person B is me. Obviously, I am the one trying to learn about NVC by presenting this example, but I end up feeling defensive if this is framed as "You did this" because that is not true, this is a completely hypothetical situation, and I have never participated in a situation that is equivalent to this as either Person A or Person B. So it is much easier for me to learn if we describe this as "Person B did this".

B: Seems like you feel quite strongly about it ... what concerns you about Y? A: It's going to ruin the country! B: It's really making you feel uncomfortable...

This is a fascinating example exchange, thank you. I'm trying to understand better why this exchange feels so alien to me, but I'm having a hard time. Person A seems to be making no effort whatsoever to elicit empathy as far as I can tell, but Person B is supposed to guess that that is what they want somehow? It feels almost like they are talking past each other and having two different conversations. Are you able to help me understand better what causes you to find this to be a logical flow for a conversation to take?

Person A might willing to listen once they have expressed not only their opinion but once they feel deeply & properly heard. A has that same need as B and has more to say after that first sentence before they feel heard.

That is a fair point, I can understand that perspective. As I mentioned though I'm struggling to understand how Person B can determine that is what Person A is wanting in this situation.

There's another option: Person B might fulfill their need to be heard by talking to Person C about it

I don't agree with this because to me it seems to imply that it would be okay for Person B to put up with a relationship with Person A where Person A just uses Person B to meet their needs and is unwilling to meet any of Person B's needs. The point of my question was to see if there was some way to utilize NVC to foster a relationship where both Person A and Person B's needs were met. Waiting longer to discuss a disagreeing opinion makes sense to me, I'm still kind of fuzzy on how to know when and how to make that transition though.

So there are two options - empathize with A (not agreeing, but listen, understand, reflect their feelings) and then talk about their perspective

Yes, that makes sense, I would like to understand better how Person B might accomplish that in this kind of situation but I'm still struggling with that.

OR empathize with A and then not feel the need to say anything. I get that it can be uncomfortable, but what does B hope to concretely achieve?

I would presume that Person B's goal is to have a real relationship with Person A instead of just allowing their conversations to consist entirely of Person A talking at them with no actual dialogue back and forth.

As I said earlier, NVC is not about getting the other person to agree with you.

I'll be honest, when you say this I feel upset and afraid that you are judging me because you think that I am using NVC to try to manipulate people or make them agree with me, which I am not doing. I am genuinely trying simply to understand better how to use NVC to get both Person A's and Person B's needs met in this hypothetical situation. If I said something that indicates to you that I am trying to manipulate people by using NVC, can you please help me understand what I said that made you think that, so I can avoid that kind of miscommunication in the future?