Spending hours or days with a group in the wilderness affords much time for asking questions and listening deeply to a person’s soul. In a week-long wilderness experience you will typically spend as much time with a person as you would during a twelve-month period of typical ministry activities back at home. As a result, people usually open up more because of spending so much time on the log. What a person offers in conversation is largely related to the level of safety they feel in the relationship.
One way to begin establishing trust in relationships is to ask good questions of others. Over the years lots of guides I know have explored questions to get conversation started while on the trail. The list below is sampling of these types of questions. Often while you are hiking or paddling, or sitting around a meal, all it takes is a good question to get an individual or a small group to open up more deeply about themselves. Hopefully this list to get you started, and please do send me along questions you’ve used as conversation starters as well!
165 Conversation Starter Questions
- What do you think are some of the pluses and minuses of social media?
- Who taught you how to drive a car?
- What kind of clothes are you most comfortable in?
- Have you ever returned a product to a store because it was defective?
- If you were to receive a text message right now, what would you want it to say?
- What was your best year in school & why?
- Have you ever invented anything?
- Name two people (living) you’d love to follow around for a few days & why.
- Did your parents ever explain to you where babies come from?
- What have you done for your last two vacations?
- Recall articles of clothing that were your favorites at one time or another.
- Name two things you love to do. When was the last time you did them?
- What’s your favorite flower to give or receive?
- If I said there was a long distance phone call for you, who would you like it to be & why.
- If I was to give you a large package, what would you hope was in it?
- How do you like to spend your leisure time?
- If you had $500, what would you do with it?
- Where did you spend the best summer of your life?
- What is your most prized possession?
- What do you like most about children? What do you like least?
- If you could whisper one statement into the President’s ear, what would it be?
- What do you like about your name?
- What would you do with a credit card for 24 hours?
- What has been the most important book, movie or play you’ve read or seen in the past two years?
- What is the most common misconception people have of you?
- Have you ever written a letter to the editor & what was the topic?
- If you were King of the world, what two things would you do first?
- Do you think the problem of global warming is being exaggerated? Why or why not?
- Where do you like to spend your vacations?
- If you could change one thing during your lifetime, what would it be?
- What turns you off?
- Have you ever carried a picket sign?
- What’s the most frustrating thing a person can do when you are talking with them?
- Tell about the funniest date or outing with a friend you’ve had.
- Which of your friends, past or present, do you laugh the most with? Why do you think this is so?
- What do you want to be remembered for after you die?
- Share one of the happiest days of your life.
- What’s something about your personality you’d like to change?
- If you had one year to live what would you do?
- What is your idea of a happy family?
- Share a phrase that comforts you.
- Complete this statement: One of the things I missed during my childhood was…
- What do you think your purpose is in life?
- What do you like about yourself?
- Is it harder for you to see good in others or good in yourself? Explain.
- Share a time when you had hurt feelings.
- What do you do when you are depressed or feeling down?
- What can you identify as a turning point in your life?
- Do you ever feel lonely?
- What’s an important goal you’d like to accomplish in the next year?
- Have you ever been broken-hearted? What did you learn from it?
- Have you ever been very ill?
- Describe someone in your family in two sentences.
- Where do you grow the most – in solitude or in relationships?
- Tell about the person who has had the most impact on your life.
- Name two people outside your family that build up your self-esteem.
- Name one event in your life you’ll never forget.
- What’s the difference between compliments and flattery?
- As a child, did you ever run away from home?
- Where do you go when you want to be alone?
- Is there a topic you would be reluctant to discuss?
- What’s something about you that you hope others will notice?
- What emotions do you find most difficult to control?
- Name something you’re proud of about your family or a member of your family.
- What is something you’ve accomplished that’s important to you?
- What do you do when you want to get out of something?
- What’s the hardest thing you’ve ever been through?
- Tell about a gift you have given and are proud of.
- Where do you go to get validated or appreciated?
- As you look at the world what is something you sometimes wonder about?
- What’s one thing you’d like to try before you die?
- What do you like most about your closest friend?
- What are two things at which you are good?
- Will you raise your children more or less strictly than you were raised?
- Name one thing you can do now that you couldn’t a year ago.
- Name one thing you want to do better.
- What do you think you will do about your parents when they get old?
- How do you show someone you like them?
- Tell about something good that has happened as a result of a choice you’ve made.
- What is one quality you would want in a friend? Why?
- When you were a child, for what did you receive the most criticism or punishment?
- Tell about something you’ve done recently that you’re proud of.
- Describe your ideal mate.
- What makes you dislike a person on sight?
- Which member of your family are you most like? How?
- What was the hardest decision you’ve ever had to make?
- What pleases you most about your parents?
- What is one of the temptations you struggle with a lot?
- What would you like to feel more confident about?
- What are three things you would change about your personality if you could?
- What are three things you are really sensitive about?
- What are three things you like to be complimented on?
- What are some things you like or brag about?
- What are three things you would change about your physical appearance if you could?
- When you were a child, what was your favorite subject in school? What was your least favorite subject?
- What one possession would you save if your house were on fire?
- It you could travel to any place in the world for one week, where would you go and why?
- It you had $1,000,000 to spend for the benefit of others, what would you do with the money?
- If you could have any four people who have lived or who are now living, to your house for dinner, whom would you invite?
- What would be your dinner topic with your four guests?
- What is your favorite time of the day?
- What is your favorite holiday?
- If you could trade places with anyone in the world for one day, who would it be?
- If you knew you had only one year to live, whom would you spend the year with?
- What ‘thing’ would you like to be remembered for by your family and friends at your death?
- How would you define joy?
- What one quality do you look for most in friends?
- What one word would you use to describe each person in the group?
- It you could receive a sixth sense, what would you want it to be?
- What do you want to be doing in ten years?
- What makes you frustrated?
- What is success?
- How do you feel about growing old(er) ?
- How would you describe peace?
- What would you like to be remembered for after you die?
- What is the worst thing parents can do to children?
- What four things are most important in your life?
- What makes a house a home?
- If you were told you only had one week to live, how would you spend it?
- What talents do you wish you had?
- How would you describe a happy family?.
- What do you most dislike about yourself?
- Complete this statement, ‘If I could live my life over again…’
- In what ways do you act like a child?
- What does courage mean to you?
- If you wrote a book about yourself, what would it be titled?
- What color do you think of when you think of happiness?
- What part of a big parade would you like to be in?
- How would you describe the ‘ideal’ father?
- What makes a ‘good neighbor’?
- What is your favorite room in your house? Why?
- If Jesus was coming to your house for dinner, what would (if anything) would you do to improve your home? Yourself? Your relationship with Him?
- Who has some influence on you and your Christian life?
- What are some of the things you fear? Love? Get angry about? Or run from?
- What does it mean to ‘bear one another’s burdens’? (Galatians 6:2)
- What are some of the things that make you feel like weeping?
- What is your definition of a Christian?
- What are your feelings about death?
- What things make your life complicated?
- What feelings do you have the most trouble expressing?
- What lifetime dream are you still trying to make come true?
- How do you feel about the way you use your money and your lifestyle in general?
- How do you feel about the whole question of time? How do you spend your time? Explain in detail.
- How is your concept of Christianity different than it was three years ago7
- What does it mean to be a spontaneous Christian?
- What’s the best way for you to share your own faith?
- Which Biblical character do you admire most and why?
- What personality trait has the Lord changed in you?
- Have you ever been persecuted for you faith? How?
- What has caused the biggest leap in your Christian growth?
- Tell about a recently answered prayer.
- Share a time when you believe that God led you?
- How is your concept of Jesus different now than it was 3 years ago?
- When was the last time you were struck with God’s faithfulness?
- What would you want a non-Christian to notice about you?
- What do you say to a person who asks if you are religious?
- Do you think the Lord would go to a dance club? a party’7 Why or why not?
- What is your favorite Bible story & why?
- In what way does your faith in God affect your life?
- How do you believe the Holy Spirit works?
- What does this phrase mean to you: ‘The Kingdom of God is within you.’ (Luke 17:21)?
- What does worship mean to you?
- At what time or period in your life were you most aware of the presence of God?
- What’s your biggest fear in going further with your commitment to Jesus?
- Have you ever been angry with God? Why?
- When do you feel closest to God? How do you tune into God?
by Ashley Denton
If you’d like to learn more about the theology, theory, and practice of outdoor ministry, Christian Outdoor Leadership is available on Amazon.
