Charity in your arguments, and the counter arguments you pose, is critically important. Many fallacies, such as strawmanning, ad hominum, and the fallacy fallacy, are often born out of being uncharitable to whoever you happen to be arguing with. Now, those fallacies often have other causes we well, but charitability is key to not allow your biases and other preconceptions to get in the way of understanding, learning about, and appreciating views different from your own, regardless of whether or not you will end up agreeing with those views. That itself is of the utmost importance because, without the ability to understand and relate to views different from your own, you will be unable to critically analyze your own beliefs effectively. Without that skill, you’re highly likely to end up thinking some of your beliefs are justified even when in truth they are not.
We should all know that disregarding an argument without actually thinking about it is dishonest. So the real question is when are we being charitable, and when are we not, and when are we handing the argument over on a silver platter? We want to be doing the first and not the other two. There is no simple answer to that question, but there is important context to take into consideration.
First, what is the context? Are you able to question the argument directly, such as in a disagreement with friends, or are you facing an argument whose primary proponents are unavailable, be they dead or otherwise difficult to communicate with? If you’re in open communication with the person you’re arguing with, then charitability become much easier. You don’t have to guess what they mean. Instead you can ask questions and make suggestions, as you should. If you don’t like a definition, then you can ask them about their use of it. Point out what you think are flaws, or even unintended consequences of using such a definition. By asking questions and point out what you see as flaws, you allow your opponent to actually answer what they mean for themselves and saves you the trouble of making those problematic assumptions.
Now if you’re not in open communication with your opponent, and if you, for whatever reason, cannot get into open communication with them, then there are two primary tactics you can take to remain charitable. You can either try to create your own interpretation of their ideas, and try to answer your questions by taking that position for the sake of argument, or you can locate someone with the same or similar view and ask them, or even debate them if they are willing. Given the option, one should ideally do both, but, given limited time, you should choose arguing someone who holds the view rather then trying to interpret it yourself as they will generally be far more charitable then you will be where you to assume the person’s meaning. However, that is not always going to be an option, so how does one interpret a view they don’t agree with, but still remain charitable?
It’s not easy, and it will never become easy. To be good at it it takes time and practice. I’m not a master of this art either, which is why I caution against it if the other options are available. But the first thing you should do when you run into unclear comments or loose ends in another persons argument is see if the answers lie somewhere else. You can do this by looking at other works by the same author, looking at defenses of that author’s views, or by looking at the works of ideally contemporary people with similar views.
By doing all that, and adding it to your own ability to defend an argument and be a devil’s advocate against your own views, you can then more safely say that you are being charitable against your opens views. Though, if you are forced to take the second route, you can’t ever truly know if your being fair, or that your interpretation is accurate. It is still your interpretation of another persons work, not their interpretation, and it is always important to remember that fact. The opportunity may come up where you can actually ask a relevant party and they might disagree with most or all of what your interpretation says, so you must remain open to that possibility.