“Did you give him the money?”
“Well, listen, here’s what happened – ”
“Did you give him the money, yes or no?”
People sometimes feel that a yes-or-no question should be answered (or answerable) with one or the other, a single word, and that anything else means the responder is being evasive.
Sometimes this feeling is correct. Sometimes there really is a simple yes or no, and they’re trying to confuse the issue.
But many times, the best answer or most direct answer isn’t a simple yes or no. The term “yes-or-no question” is, in fact, misleading. There are plenty of perfectly valid responses not covered by either word. Responses like…
A clear answer exists, but you refuse to give it.
Maybe the answer would compromise your privacy, someone else’s trust, national security, or any of a million other interests.
Maybe answering would set a bad precedent (e.g., the answer is in the FAQ, and you don’t want to keep re-answering it forever).
Maybe you just don’t feel like answering, and you don’t need a specific reason, because the questioner is Not the Boss of You.
A clear answer exists, but you’re not certain what it is.
Maybe you have no idea.
Maybe you have a good guess, but you’re not 100% sure. Maybe the source for your answer isn’t entirely reliable.
Maybe the answer theoretically exists, but is unknowable at this time (e.g. “Will it rain three weeks from today?”).
Maybe you don’t know right at the moment, but given some time, you could look it up or figure it out.
No clear answer exists; the answer is undefined.
Is fan fiction legal in the U.S.? It isn’t just that you don’t know the answer; the answer literally does not exist. It depends on a judge’s interpretation of a law, and that interpretation has not yet been given.
The question is defective in some way.
Maybe the question is ill-defined. (“Is this the best way to get to Cleveland?” “Well, what do you mean by ‘best’? Do you mean fastest? Easiest? Cheapest?”)
Maybe the question contains a false assumption. (“Have you finished writing the Sandburg Report yet?” “Uh, you didn’t assign that to me.” Technically “no” would be the correct answer there, but it’s certainly not the best answer.)
Maybe you need more information to answer the question; “It depends.”
The answer is complex.
“Are your students doing their homework?” “Well, the majority are pretty consistent. Several have struggled in the past, but they’re getting better. Amy and Tristan haven’t turned in a single assignment all year.”
A literal, unqualified yes or no would be misleading.
“Do you think we should outlaw these horrible activities?” “No…because I think existing laws prohibit them already, and we can fight this most effectively by enforcing the laws we have.”
You are unable to process the question.
Maybe you didn’t hear what they said.
Maybe you’re too tired, confused, or drunk to come up with a good answer.
Maybe the question is too complicated for you to understand.
Maybe English (or whatever) isn’t your first language, and you’re still trying to figure out what they asked.
Obviously the list above is not exhaustive, and many questions or situations could fall under multiple categories. But I think the point is clear: yes-or-no questions are not always yes or no. It’s a false dichotomy – like most dichotomies are.
Love the complexity. Embrace the fuzzy.
Brian D. Buckley 
But in your first example, while it’s possible the answer could be more complex, the best answer is most likely yes or no. Perhaps “I tried but he wouldn’t take it.” But most likely not.
Sure, in many (most?) situations, that question could reasonably be answered with one word. But, as you mentioned, it’s also quite possible that it couldn’t be; it all depends on the situation. The main point is that demanding a one-word answer immediately (as the questioner did in that example) is rarely a smart thing to do.
A friend of mine went to a big dinner event once for his job. He was giving a presentation of some sort, and (he found this out later) a woman from another department was quite taken with him and asked another co-worker if my friend had a girlfriend.
The literal answer was no, he did not, but the actual, and much more helpful, answer was, “No, he doesn’t have a girlfriend, but that’s his wife sitting over there.”
Haha, that’s great.
Of course, I personally consider my wife to *also* be my girlfriend… 🙂