" 4) "If your house was on fire and you only had enough time to save 3 items, which 3 things would you pick?
" 5) "If you could create a dream job where you got paid to do something that you're extremely passionate about, what would that job be?
Things like "favorite childhood cartoons", "weirdest halloween costume you wore as a kid", etc.
Another strategy is to have a few interesting news stories ready.
After sitting down at the table and introducing yourselves to each other, look at your date and say something along these lines (playfully, with a smile): So, I've decided not to ask you what kind of job you have, or what you like to do fun.
Instead, I'm gonna try to get a feel for your personality, based upon your answer to a hypothetical question." So at this point, you've caught her attention and set yourself apart from everyone else.
You're also demonstrating that you're interested in getting to know her personality instead of just being interested in her for her looks.
It will make the woman feel like she needs to impress you, instead of you trying to impress her! Try to relate it to some of your own interests (sports, music, travel, etc.), so that you can extend the conversation after she answers the question.
What is it specifically about Japan that you're drawn to? ;) Do you mainly listen to Rock, or are you into other styles of music as well?
" From this point, you can just allow the conversation to develop naturally, by taking her answers and forming new questions from them.
Maybe you read an article last week about a monkey who taught himself how to ride a bike, or a man who lived for 6 months without eating any food.
Keep the conversation going and before you know it, the 5 minutes will be over.
Here is an example: "Let's suppose you get a phone call tomorrow morning telling you that you've won a free trip anywhere in the world to watch a musician of your choice perform in concert.