What is the most trouble that you got into at school? If you could do high school all over again, would you?
What is the longest amount of time that you spent in another country? If you could live anywhere in the world, where would it be?
Or you might realize that this person is not right for you. Even if you are already with someone, it is always great to try and get to know them better.
Whether you have been dating for a month or a decade, it does not matter.
What is something you have done that you would never do again?
What is the first website that you go on at the beginning of the day? Besides your e-mail, what are 3 websites that you always check every day? Do you think that you spend more than 1 hour a day on the internet?
They make great ice breakers when you are meeting new people as well. Ask the person that you are interested in a few of these questions.