Is it correct to say "With whom do I have the pleasure of speaking with?"

Question

To address a common mistake in everyday speech, especially with customer service representatives and other professionals..

Answer 1

The phrase "With whom do I have the pleasure of speaking with?" is grammatically incorrect due to the repetition of the preposition "with." The correct phrasing would be:

"With whom do I have the pleasure of speaking?"

This version eliminates the redundancy and maintains proper grammar.

Answer 2

Having the word "with", in a sentence more than once, makes it grammatically incorrect. There are two possible ways to reword this. You could say either;

"To whom do I have the please of speaking with?"

OR

"With whom, do I have the pleasure of speaking to?"

As both of these are questions, it does not matter if you use a preposition (in this case the word "with") at the end of it or not. If you were to diagram each sentence to see if they were grammatically correct, the word "with" would end up in the same place for both, making the sentence align with proper grammatical rules.

Answer 3

No, you are using "with" twice:

Correct: With whom do I have of speaking"

Answer 4

"With whom do I have the pleasure of speaking with?" is incorrect. We have 2 ways to use this phrase correctly, but this way of saying it needs to make up its mind.

The common phrase used in society is "Who do I have the pleasure of speaking with?"

The proper phrase that is grammatically correct is "With whom do I have the pleasure of speaking?"

"With" is a preposition, and it is grammatically improper to end a sentence with a preposition. When you use it properly at the beginning, that's it; no need to repeat it.