マイケルsan, Wes-san, kon'nichiwa!
Since the question is VERY polite, it's definitely ok for Japanese people to be asked like that.
Of course, there're people who try not to speak too much about themselves (especially in the area centering Tokyo), and just reply very ambiguously. In such case, you can just stop there and don't ask further questions!
I don't really like those kind of people, but it's one of the characteristics in this area. So, if you come across situation like that, it's not because you're foreign person, but it's their issue
No worries!
These kind of questions shown on the programme is very useful and yet we never learn at beginner lessons of any foreign country.
It's simply because most of the courses are based on grammar, and this kind of sentences are for "survival" conversation like.
Yet, even in survival conversation, it's not really necessary for "survival", so almost impossible to find it.
Those are like in between: rather, those who want to try the foreign language s/he is learning with very limited knowledge.
It's a very new attempt and you nailed it perfectly!!
Looking forward to the next programme!
Natsuko(奈津子),
Team JapanesePod101.com