"Whenever I speak to groups of parents, I say, 'If you do only one thing differently after tonight, I hope you'll try back-and-forth questions. It will enrich your family relationships and teach your children the art of conversation — a gift that will last a lifetime.' . . .
"The best questions are open-ended and can't be answered with just a word or phrase. 'What's something good in your life that's happened since we last saw each other?' is a better question than 'How's it going?' (which typically evokes something like 'Pretty good') or 'What's new?' ('Not much').
"Most of the open-ended questions below can be used in one-on-one conversation. Other questions or topics such as, 'What do you wish we did more often as a family?' or 'Who has a problem that the rest of the family might be able to help with?' are more appropriate for family meals or a family meeting."
40 Conversation Starters
"1. What was the best part of your day and why?
2. What was the best and the worst part of your day?
3. What's something nice you did for someone today?
4. What's something nice someone did for you?
5. What is an act of kindness you saw someone perform this week?
6. What is an act of kindness we could each do tomorrow?
7. What is something you learned today in school or from life?
8. What happened today that you didn't expect?
9. What was an interesting conversation you had today?
10. What's something you accomplished this week that you feel good about?
11. What's something you're looking forward to?
12. What are you grateful for today?
13. What's something you're worried about?
14. What some good news that you haven't shared yet?
15. What's the hardest thing about being your age? The best thing?
16. What are two goals you have this week? This month? This semester? This year?
17. What is something that someone in the family did for you recently that you appreciated?
18. Who has a problem or challenge that the rest of the family might be able to help with?
19. If you could be granted three wishes, what would they be?
20. What are two things other people can do to make you happy?
21. How can somebody help you get out of a bad mood?
22. What does 'success' mean to you?
23. What does 'being in love' mean?
24. How do you know if someone is the right person to marry?
25. What is something you did during the past year that took courage?
26. How do you know if somebody is a true friend?
27. Who is someone you really admire?
28. If you had $100 to give to a charity, what charity would you give it to and why?
29. If you could talk with anyone from history, who would it be? What would you ask them?
30. If the house were on fire, what would you try to grab on the way out?
31. If you were President, what are two things you'd try to change?
32. What do you wish we did more often as a family?
33. What is a way you've changed in the past two years?
34. If you could change one thing about yourself, what would it be?
35. What do you wish you were better at, or would like to learn how to do?
36. Moral dilemma discussions: Read a letter to an advice columnist but not the answer — until everyone has had a chance to say what advice they would give.
37. Bouncing question: One person asks another a questions (such as any on this list), then that person asks someone else a question, and so on until everyone has been asked a question. (If you don't wish to answer a particular question, you can request another.)
38. One-word topics: Choose any topic (school, teachers, sports, TV, news, movies, books, friends, heroes, God, prayer, decisions, music, politics, etc.). Anyone can say anything about the topic that comes to mind.
39. What was good about your trip? When someone comes back from an experience (a trip, summer camp, etc.), each family member asks the person a question about it. ('What were two highlights?' 'How was it different from what you expected?' 'How did it affect you as a person?')
40. Are you more like a rose or a daisy? In what way? More like a dog or a cat? The city or the country? A lake or a brook? Choose one pair and invite everyone to answer."