Most of our conversations happen at a very sterile, arms-length level.  We may not know people who we’ve been friends with for decades very well because we stick to discussing the results of the weekend’s game or what’s happening at the kids’ school.  Maintaining shallow relationships makes it difficult to engage in serious topics like the need for God’s forgiveness and our depravity before Him.  As you engage with friends begin to weave in more intimate questions that really get to the heart of who they are and what they care about.  The list below was compiled to provide you with some ideas.  The questions start out less revealing, but require more vulnerability as you go down the list.  After both you and your friend or family member open up to more meaningful discussions, you can turn some of the answer to the questions toward Jesus and how He solves our need for forgiveness.  Alternatively, discussing the themes and/or characters in a book or movie can lead you to topics which provide a transition asking about one’s belief in God or basis for their moral positions.  Either way, the idea is to get past the small talk and connect with them that you might ultimately tell them about Jesus.

Four simple questions

• What’s the besting thing going on in your work/family/life?
• What’s the worst?
• How does that affect you?
• What can I do to help?

Complete list of questions

• What do you believe are the most important inventions in the past 100 years?
• What do you think are the most significant problems in the world?  What is the primary source of those problems?
• What will the world be like in 10 years?  Will it be better or worse off?
• What were the key turning points in history?  Which event would you most want to change?
• What quote, proverb or Bible verse is most meaningful to you?
• What career would you be the best/worst in?  How did you get started in your career?
• Who are your heroes?  Who is your favorite author?  musician?  athlete?
• What is your favorite place to travel and what do you like to do there?
• If your house caught on fire and you could save one thing beyond family or pets, what would it be?
• If you could gain one quality or ability, what would it be?
• What movie or book characters do you most identify with?  What do you find most admirable and vexing about this character?
• What do you think have been the most influential books in history?
• Who do you admire the most?  What religious leader to you admire most/least?  Who do you believe Jesus is?
• What do you think God is like?
• What do you regret not doing or learning to do?
• Who has influenced you the most?
• Who have you influenced the most?
• What is your best memory?
• What are you most passionate about?  What is the source of that interest?
• What do you spend your free time doing?
• What do you know about more than anything else?
• What have you dreamed of doing, but haven’t done?
• What are the most significant risks you’ve taken?
• What events have had the most influence on your thinking?
• What is your philosophy of life?
• What have you changed your mind about recently?
• What do you pray about most?
• What’s the most interesting/challenging dilemma or decision you’ve faced lately?
• What was the biggest decision in your life and how did you approach it?
• How do you make judgements about good or bad, right or wrong?
• What have been the most critical points in your life?
• What was your greatest success / failure?
• What is your greatest need?
• If you could relive or redo a day in your life, what would it be?
• What do you have most difficulty forgiving yourself for?
• What do you think happens after you die?

A few of the questions have been derived from this list about bonding with others and the background information in this article.