99 Wondering Questions

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Many times we are never more than a few wondering questions away from a good spiritual conversation.

With the right attitude and atmosphere, any of the following 99 questions can be powerful tools. Remember, however, that the best questions always come from the wondering that the Holy Spirit is stirring inside of you as you listen to others. Listening leads to wondering, and wondering provides more opportunities to listen. As you grow in your ability to harmoniously balance God’s teeter-totter, spiritual conversations will flow more naturally in your day-to-day life.

• I’ve made it my lifelong goal to learn from others; what’s the greatest lesson you feel you’ve learned so far in your life’s journey?
• Tell me about your greatest success and your greatest failure along the way.
• Would you mind sharing with me the greatest piece of wisdom ever passed on to you?

• What prompted you to pursue your career in _______________?
• What do you like most about what you do? least?
• Do you see this as a lifetime career, or a steppingstone to something else?

• If someone wanted to talk to you about God, how would you like to be approached?
• Have you ever had anyone approach you and try to talk to you about God?
• What kinds of feelings were you left with after the encounter?

• What images or words come to your mind when you hear the word evangelism?
• The word evangelism means “to proclaim good news.” If that’s true, why do you think this word carries so much baggage with it?
• If you were asked to describe the good news that evangelists are supposed to be sharing with people, how would you describe it?

• What is your dream job?
• Are you working toward it already? If not, what is standing in your way?
• What advice would you give to a young person about finding vocational happiness?

• What kind of exposure did you have to religion when you were growing up?
• Why do you think there are so many different religions?
• Do you think it’s possible for all religions to be equally right? Why or why not?

• What conclusions have you come to concerning life after death?
• Do you think it’s possible to be certain about where you’ll spend eternity?
• Have you ever explored what the Bible has to say about eternal life?

• Have you ever been able to get a handle on what you think your purpose in life is?
• Everyone seems to agree that money by itself can’t buy happiness. What, in your opinion, does guarantee a happy life?
• In what ways do you feel you’re really winning or losing at life?

• Do you consider yourself to be a Christian?
• Based on your understanding, how does someone become a Christian?
• Have you ever explored what the Bible has to say about how someone becomes a Christian?

• How did 9/11 affect your view of God and the world?
• As you’ve watched or read the news, what conclusions have you drawn about the nature of humanity?
• Do you believe there is a solution to social problems such as rape, murder, famine, war, racism, and divorce?

• Have you ever had an experience in which you felt the presence of evil?
• Have you ever had an experience in which you felt the presence of God?
• In what ways have you seen good and evil played out in your life?

• What causes you to struggle the most with the idea of God’s existence?
• Up to this point in your life’s journey, have you met anyone or experienced anything that made the reality of God seem plausible to you?
• To what do you attribute your disbelief in God?

• It sounds as if you value open-mindedness. Do you ever find yourself closing your mind to certain things, ideas, or people?
• What criteria do you use to determine whether something is true?
• Does your worldview allow for any absolutes?

• How did you meet your husband/wife?
• What have you learned about yourself through marriage?
• What do you enjoy most about marriage? least?

• Has your understanding of the word love changed over the years?
• Why do you think so many couples end up falling out of love?
• If you could pass along one word of advice about how to keep a relationship going and growing, what would it be?

• Why do you think so many people prefer to live as if God does not exist?
• What would you want God to do to validate his existence and bring you to belief?
• It’s been said that many people never find God for the same reason a robber can’t find the policeman standing on the corner; what does this saying mean to you?

• Some people believe that we are the product of a random evolutionary process. Do you think discussions about right and wrong have a place in that kind of worldview?
• How do/will you teach your kids right from wrong?
• What authority do you appeal to?

• Did you have any dreams or set any life goals when you were younger?
• What dreams have you let go of?
• What dreams are you still hanging on to?

• Are you optimistic or pessimistic about the future of our world?
• Do you think it’s easier or harder to raise kids in today’s world than it was when you were growing up?
• What concerns you most when you think about your future?

• What experiences have shaped your worldview the most?
• Has there been one book or movie that’s left its mark on you in a significant way? How so?
• Besides your parents, is there any one person who stands out as having had a major role in shaping your life? Tell me about him or her.

• God has changed my life; have you ever considered letting him change yours?
• If God had his way with you, what do you think he would change first?
• What scares you the most about letting God change your life?

• What three principles of life have benefited you the most so far in your life’s journey?
• What, if anything, causes you to be hopeful about your future?
• If you had only six months to live, what would be on your list of things to do before you died? Why?

• As people get to know you, what about you do they enjoy most?
• As people get to know you, what about you do they enjoy least?
• As people get to know you, in what area do you feel most misunderstood?

• How would you describe your leadership style?
• What leadership style do you respond best to?
• Jesus was described as a servant leader. When have you, if ever, experienced that kind of leadership?

• Why do you do what you do?
• What life experiences have molded you and motivated you to pursue the path you’ve chosen for life?
• If you were to choose your path over again, would you choose the same one? Why or why not?

• If you could ask God three questions, what would you ask?
• If God were to ask this one question, “Are you for me or against me?” what would you say?
• What evidence would you present to defend your response?

• Which gender do you think has the tougher path in life?
• What do you enjoy most about the opposite sex?
• What do you enjoy most about being male/female?

• Have you ever hated anyone?
• Has anyone ever hated you?
• Have you ever been able to overcome hatred? If so, how did you pull it off?

• If you could choose the manner of your death, how would you like to go?
• How would you like to be remembered at your funeral?
• Does the thought of death scare you?

• It’s been said that life is largely out of our control. If that’s true, why do so many people try to control the uncontrollable?
• Do you struggle with trying to control things?
• What kinds of things do you think can be controlled in life?

• What kinds of habits do you struggle with most?
• Do you ever find yourself doing the very things you don’t want to do, or not doing the things you really want to do? If so, what do you attribute this to?
• Have you ever found anything to set you free from this cycle?

• How would you change the way you were raised?
• What things are you doing/going to do to raise your kids differently?
• What values from your childhood do you want to pass on to your kids?

• If Jesus were here right now, what would you ask him?
• How do you think he would answer?
• How would you feel if that happened?