didn't used to and didn't used to have been

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Didn't used to have been? No, it's a complete mess.

Firstly, it should be "didn't use to."

Secondly, "have been" refers to your experiences, such as "I have been to Paris."

"Used to" or "didn't use to" refers to a specific period in the past. "I used to be a chef;" "That supermarket didn't use to be here."

The two structures are used for two different and incompatible meanings. You can't have an experience that only applied in the past, since experiences last forever.
 
If you refer to the following link Learning English | BBC World Service ,you're going to see that "didn't used to" and "didn't use to" are possible. Would you be still saying that "didn't used to" is incorrect?
 
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If you refer to the following link Learning English | BBC World Service ,you're going to see that "didn't used to" and "didn't use to" are possible. Would the author be saying a complete mess too?
Don't ask for our opinions and then produce another opinion with the suggestion that ours are wrong.
 
I'm getting fed up with you testing us in this way, ostap.
 
It's fairly simple. "Use to" and "used to" sound exactly the same, so it's a common mistake to write it as "didn't used to." So basically you're asking a philosophical question as to when a common mistake becomes accepted English.

But that doesn't change the fact that there's not a single native speaker in the world that would use the phrase "didn't used to have been." In fact Google it, and the first result that comes up is the page you linked to and the second result is this page.
 
You're right about "didn't used to have been". I've searched for examples of "didn't used to" on COCAE . It gives 126 examples.
 
If you refer to the following link Learning English | BBC World Service ,you're going to see that "didn't used to" and "didn't use to" are possible. Would you be still saying that "didn't used to" is incorrect?

But even Roger Woodham admits that "didn't used to" is less common than "didn't use to".

For questions and negative forms, two forms of the verb are used - either the normal infinitive pattern after did (more common), or the past form used (less common).
 
If you're still not a teacher, you would most definitely become a good one.
 
I'll confess that I was well into adulthood when I realized that "Didn't used to" is wrong, but I'd been using it consistently all my life, for exactly the reason stated - it sounds the same as "didn't use to" and I didn't apply the "with a form of 'to do' you keep the bare infinitive form." Instead it was "used to/didn't used to" in my brain.

However, once I became aware of my error, I stopped immediately. I would never try to justify it as "common use." Mistaking "infer" and "imply" is common use, but that doesn't make "What are you inferring by making that remark?" correct.
 
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