In case the query was not only an example, but also a true question, I'll get into it separately.

stating the question as positive assertion: "A man can understand a woman's perspective on non-shared experiences, such as gestation or historical oppression".

first, we explore my justification for the belief and determine if it is valid: I offer no justification whatsoever, since I do not think the statement is true in its current form.

so, I state the negation: "Nah, men can't really understand what it's like to carry a baby or how women view their historical place in society".

My justification for this is based on a particular use of "understand", which might vary from yours, so you might start by asking me to clarify any terms that might cause contention at the outset, or you could just ask me my reasoning at the outset and solve linguistic misunderstandings as we progress in the discussion.

Epistemology is about the nature of knowledge, yes, but it covers a wide range. I would say that your query and the follow up commentary are definitely within the realm. To be specific, Epistemology generally discusses the truth value of Assertions, and the methods by which one could determine them to be "true" in a meaningful sense.

In basic terms, how do we separate "justified true belief", which is one concept of knowledge, the idea that for it to be knowledge it must 1) be true, 2) have rational justification for acceptance and 3) be accepted.

Is it possible to understand a member of the opposite sex? it depends on what you mean by understand, but in Epistemology you'd ask "can I have a justified true belief about the mental state of a person whose brain works differently than mine?" to be clear, I think, if i understand the question at hand.

The other thing is, are you asking that question, or just using it as an example?

As for as transcending personal difference, yes, it should. Truth is, at the core of definition, "consistent with reality". In fact, epistemology seeks directly to transcend those differences by establishing and understanding of what we mean by "true", and as stated before, methods for determining truth.

Street Epistemology is basically methods you might use in conversation to question the truth of a statement made by someone, or to help them question it without confrontation. Ways of thinking about things or discussing things to bring to light whether a person has a "justified belief", and also ways of determining the truth value of that belief, which is "true", "false", or "indeterminate", meaning that there is no way to determine which of the two values it has given current knowledge.

Hope that wasn't too wordy, I know it was too repetitive but I'm having a rough week and it's close enough that editing isn't appealing to me.

I agree there should be more chitter chatter and yes, men understanding women would be a great place to start. What's your query?