I asked a friend of mine "Does he use workout machines that tone your ass?"
I know it's more clear if I had said "Does he use workout machines that tone his ass?", but is the first question still correct and convey the same meaning as the latter?
I asked a friend of mine "Does he use workout machines that tone your ass?"
I know it's more clear if I had said "Does he use workout machines that tone his ass?", but is the first question still correct and convey the same meaning as the latter?
They are usually the same. The generalized "you" in English behaves like "on" in French, except that there is the danger of confusing it with a specific you. (As an example, if you criticize a friend by saying "That's the sort of thing you miss," it could equally mean it's the sort of thing everybody misses. But I digress) In the case of your original sentence, it is barely possible that the machines tone your friend's ass, but not that of the party you were discussing. And yes, the distinction in the second case would be that you would stress "your" to make it clear which possibility is being invoked.
As @Jim pointed out in the comments, in the exchange:
You should try a session with my trainer, he's got a whole bunch of machines that tone pretty much every muscle you have.
Oh really? Does he use workout machines that tone your ass?
the sentence "Does he use workout machines that tone your ass?" is both perfectly grammatical and sensible.
However, in that sentence, the referent of "he" and "your" are distinct; while "your" refers to the general "you" you're seeking, "he" is the trainer, not the guy with the nice ass.
The situation would be different in this exchange:
Man, have you seen Jim's ass? It's amazing!
Oh really? Does he use workout machines that tone your ass?
While comprehensible, the response doesn't quite work (at least to my ear). Rather, I'd expect you to say:
Does he use those workout machines which tone your ass?
Which, expanded, reads "Does he use those type of workout machines which tone your ass?". Here, the referent of "he" is indeed Jim (the guy with the nice ass), and your continues to work fine as a "general you": you can tell because you could easily substitute one's (one can tell because one could substitute one's :) ).
Note there's a subtle difference between the two sentences, now:
Does he use those workout machines which tone your ass?
Means, does he use a particular type of machine?, whereas
Does he use workout machines that tone his ass?
means does he use machines in order to achieve the particular effect of toning his ass?, or, more concisely, use machines to tone his ass?.
The first focuses on the machine he uses, the second focuses on the effect he gets.