Offering a tidbit of personal information can help the other person to feel more comfortable opening up to you. Knowing how to start a conversation is an incredibly valuable skill, and like any skill, the more you do it the better you get. If you found out that you were bankrupt one day with a family to fend for, what would you do? Sometimes a random question is the best question. Don't forget to have fun. What do you think is the key to good parenting? Some of the questions will make you think.
If you could meet a famous dead person, whom would you like to meet?
100 Serious Questions You Should Ask Your Boyfriend
Elaborate on long distance relationships. After me, who is your closest female friend? This conversation gets the imagination flowing. People like hanging out with someone who can keep them on their toes. This question is great because it requires zero effort to answer, and it can lead to other conversations about food.