I think the most important skill in a modern world is listening to others’ experiences. Sometimes words can be embedded in contexts that are very different from contexts we’re familiar with, and yet that doesn’t necessarily mean we should stop using them. Occasionally, the historical trauma around a word is so great, or the connotation so universally negative, that I agree the ethical thing to do is to just never say/use the word(s).
That said, I’ve also learned that being too cautious has its downsides as well. If we allow only negative embeddings to influence the global allowability of a word, all words become more and more “off limits” as we become more aware of any context in which the word may be offensive. The world is a very, very large place, and there is a good chance that any chosen word can pick up meaning in some circles that is not intended by others.
As an example, I’m Canadian and in my family circle, “little monkey” was a term of endearment. My grandpa used to smile and show his acceptance of me when using that term as he acknowledged that as a kid I had a lot of energy and loved to climb and play upside down. I’ve since learned that in the USA there is a common context in which this has been applied to black people in a disparaging way–comparing them to a “less than human” status. There was a story on Reddit this year where a Canadian dad used this term of endearment towards his son in a playground, and a black woman who overheard this took offense. She accused him of some unkind things by assuming his intent. So in this case, someone who was trying to enforce the negative context of a word as the only legitimate interpretation was inadvertently hurting someone with no ill intent (and speaking to his own child).
Personally, I don’t think talking about flirting and beer, or reference to dead beef crosses any lines, but I’m open to listening and understanding. I don’t have a perfect solution to the context-switching problem of word use, but I think we can often mitigate damage just by showing we’re open to hearing another’s fear, hurt, or anger. Sometimes that’s enough; other times, more action is required.