Can "would" be used twice in an English conditional sentence and still be grammatical?

Question

I know how conditional *if* clause sentences work. I'm aware of the rules which I have to follow. However, I sometimes use *would* after *would* which of course is incorrect in terms of grammar. **Is there any example where you could use *would* after you had already used *would* in the first clause?** For instance: >If I would be rich, I would definitely buy a car. I know that it should be >If I was/were rich, I would buy a car But I am asking for an example where *would* after *would* would be appropriate.

Answer 1

In fact, some teachers of English take the position that your example, "I would not have told you that if would have told me what you were going to do" is incorrect and ungrammatical (even though a lot of people speak this way). A more acceptable version is:

"I would not have told you that if you had told me what you were going to do."

Answer 2

It definitely can be grammatically correct to use would twice in a sentence, but it isn't common simply because it isn't typically how people speak, or it would be superfluous. Here's an example: "I would not have told you that if you would have told me what you were going to do." Although this works, it doesn't exactly flow smoothly, and there are generally better ways to word the sentence.