Is it common to put "how old" in the middle of the sentence like this?

Native speaker’s answer

Rebecca

"How old" is in the middle of this sentence because he is asking a "trivia" question. Therefore, he is wording the question as though the two women are supposed to answer the question by filling in "how old" with the answer. For example, their answer is expected to be something like "Chandler was nineteen years old when he first..." Putting "how old" in the middle of a sentence like this is not common in general.

How do native speakers use this expression?

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