That's unfortunate because many of the most difficult and interesting discussions, philosophical or otherwise, boil down to the meanings of English words.
I have to disagree. I do a lot of pseudo-philosophical and non-philosophical arguing (my s.o. is a philosophy student), and I've realized that, as years have gone by and I've gotten better at this type of discussion, the best first step is to precisely define what each word is assumed to mean in that context and then proceed to arguing what does that mean to the topic at hand.
As a counter example, I was greatly unnerved the other day at watching a bar discussion between two friends that revolved on whether or not one could make money daytrading. Friend A said "obviously you can't, the market is random", while friend B insisted that "well, with mathematics you can predict the way it will go". This went on for hours (I refused to join) while they both had clearly very different meanings for the words "random", "luck" and "mathematics". I believe that, had they stopped early enough to define those terms, they wouldn't have argued.
Of course, sometimes the discussion is specifically about the definition of a few key words. Even then, I find what really helps is agreeing on some restricted definitions for other "primitive" words and using those primitives to build up definitions for the words in question. For example, person A could argue that selfishness is actually a form of blindness, while person B insists that it is not really so, and one can be selfish while seeing what others are doing. This way they can argue, by having pre-defined what "blind" "see", etc mean in this context.
Discussions about the meaning of words are easily just philosophical traps where one person says A and the other hears B.
I don't feel discussions that break down to the meanings of English words are interesting. Scholasticism went out of favor in part because proving things based on the assumption that Aristotle or the Bible is correct does not help once you question the source. And arguments based on the definition of "is" are also built on a shaky foundation.
Keep pulling and you have two options. You can base things on what you observe, which leads to science, or what you on things you assume which leads no where when others don't agree to the same assumptions. It's only when people have the same assumptions that you can have really interesting discussions such as Math or a good logic puzzle.
As a counter example, I was greatly unnerved the other day at watching a bar discussion between two friends that revolved on whether or not one could make money daytrading. Friend A said "obviously you can't, the market is random", while friend B insisted that "well, with mathematics you can predict the way it will go". This went on for hours (I refused to join) while they both had clearly very different meanings for the words "random", "luck" and "mathematics". I believe that, had they stopped early enough to define those terms, they wouldn't have argued.
Of course, sometimes the discussion is specifically about the definition of a few key words. Even then, I find what really helps is agreeing on some restricted definitions for other "primitive" words and using those primitives to build up definitions for the words in question. For example, person A could argue that selfishness is actually a form of blindness, while person B insists that it is not really so, and one can be selfish while seeing what others are doing. This way they can argue, by having pre-defined what "blind" "see", etc mean in this context.
Discussions about the meaning of words are easily just philosophical traps where one person says A and the other hears B.