Did you mind me asking you about your family?

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tufguy

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1) Did you mind me asking you about your family?

2) Did you mind my asking you about your family?

3) Would you mind me asking you about your family?

4) Would you mind me asking you about your family?

Answer: Yes I minded that.

Please check my sentences. What is the difference between "me asking" and "my asking"?
 
Your response works for the first two. 3 and 4 need "Yes, I'd mind it."

Either "me" or "my" is okay with no difference in meaning.
 
Yes, I did/would and No, I didn't/wouldn't are the natural answers IMO.
 
What is the difference between "me asking" and "my asking"?

I think it's hard to see a semantic difference in your particular example, tufguy. But consider these:

(a) Would you mind me smoking?
(b) Would you mind my smoking?

The underlined phrase in (a) goes by the name of the ACC-ing construction in contemporary syntax. H. W. Fowler named it the "fused participle" construction about a hundred years ago, and he considered it illegitimate, at least in his dictionary of usage. (The Kings English, published earlier, seems to allow for it in special cases -- e.g., a picture of him smoking.)

Whatever the true syntactic nature of the ACC-ing construction turns out to be -- the jury appears still to be out on exactly what it is (I analyze it as a nonfinite clause) -- it differs from the syntax of the underlined phrase in (b), which goes by the name of the POSS-ing construction and is a noun phrase or determiner phrase.

Although both (a) and (b) can arguably be substituted in a wide variety of cases, I find (a) ("Would you mind me smoking?") to be very natural as a substitute for "Would you mind it if I smoked?" (I'm not smoking now, but am considering it), or in a context where I am being contrasted with someone else, in which case "me" could even be emphasized: "Would you mind me smoking?"

The POSS-ing construction ("Would you mind my smoking?") would, on the other hand, be the better choice, in my opinion, in a case where I already am smoking or am already in the habit of smoking. In the context I have in mind, the question is implicitly conditional and could be expanded as such: "Would you mind my smoking (if I went across the street)?"

P.S. This is just an example. I don't smoke (though I did for a long time) and would never recommend it to anyone.
 
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