Here is a list of topics that can lead to good conversation at most tables. First, things to avoid:

Avoid superficial topics. “What makes you smile?” sounds sweet but there’s nothing there, it just invites platitudes and competitive humblebragging.

Avoid questions about places. At least at the tables I sit out it’s too easy for people talking about their vacations. If you enjoy that sort of thing godspeed, but I’ve had quite my fill of vacaton stories.

Avoid penetrating questions. “What do you love about yourself?” may sound like it’s bursting with positivity, but its personal enough to make people uncomfortable. Even if it the person being asked is comfortable with it they’re likely to end up bragging or telling a sob-story—neither of which makes for good table talk.

Avoid clichés. “If you could tell your younger self one thing, what would it be?” is so overplayed you’ll sound like a robot trying to start a story. Likewise with “Describe the last year of your life in 6 words or less”.

Onto the topics. This is a work-in-progress.

Your past

1. Have you changed in the last five years?
2. If you could relive one day, which would it be?
3. How much have you controlled the course of your life?
4. What book has influenced you most?
5. Can you do something today that you couldn’t a year ago?
6. Have you learned anything that’s changed how you live?
7. What did you want to be when you grew up?
8. What have you lost interest in?
9. What is the most you’ve ever feared for your life?
10. What is the defining moment of your life thus far?
11. What is the most enjoyable thing your family has done together lately?
12. What is your earliest memory?
13. What is your happiest childhood memory?
14. What life lessons did you have to experience firsthand to fully “get it”?
15. What act of kindness were you once shown that you will never forget?
16. What was the last thing you strongly argued about?
17. When was the last time you tried something new?

Your future

1. In twenty years, what do you want to remember?

Other people

1. What does it mean for someone to be educated?
2. If you could instill one bit of advice in a newborn’s mind, what would it be?
3. If you looked into the enemy’s soul, how would it be different than yours?
4. Is it more important to love or be loved?
5. What is the number one quality that makes someone a good leader?
6. What simple fact do you wish more people understood?
7. What’s something you know you do differently than most people?
8. Why do we idolize sports players?

Life

1. What are you sure of in your life?
2. What gets you excited about life?
3. What is the difference between living and existing?
4. What life lesson did you learn the hard way?

What you think

1. Can there be happiness without sadness?
2. Do you think crying is a sign of weakness or strength?
3. How would you describe ‘freedom’ in your own words?
4. If you had an opportunity to get a message across to a big group of people, what would it be?
5. If you had to pick a book that every high school student had to read, what would it be?
6. Is beauty objective?
7. Is it possible to lie without saying a word?
8. Is there such a thing as perfect?
9. What are the primary components of a happy life?
10. What are three moral rules you will never break?
11. What gives your life meaning?
12. What is a belief that you hold with which many people disagree?
13. What is important enough to go to war over?
14. What is the best part of growing older?
15. What is the difference between falling in love and being in love?
16. What is the difference between innocence and ignorance?
17. Who or what is the greatest enemy of mankind?

How you live

1. Are you more like your mom or your dad? In what way?
2. Do you ask enough questions or do you settle for what you know?
3. How do you spend the majority of your free time?
4. Other than money, what else have you gained from your current job?
5. What artistic medium do you use to express yourself?
6. What do you have that you cannot live without?
7. What do you know well enough to teach to others?
8. What do you love to practice?
9. What job would you never do no matter how much it paid?
10. What’s been on your mind most lately?
11. What’s something you don’t like to do that you are still really good at?
12. When do you feel most like yourself?
13. When you have a random hour of free time, what do you usually do?
14. When you think of ‘home,’ what, specifically, do you think of?
15. Where do you spend most of your time while you’re awake?
16. Where or who do you turn to when you need good advice?
17. Which activities make you lose track of time?

Favorites

1. What is your favorite fictional story? (novel, movie, fairytale, etc.)
2. What is your favorite quote?
3. What is your favorite smell?
4. What is your most prized possession?

Hypotheticals

1. If I gave you $1000 and told you that you had to spend it today, what would you buy?
2. If a doctor gave you five years to live, what would you try to accomplish?
3. If someone could tell you the exact day and time you are going to die, would you want them to tell you?
4. If the average human lifespan was 40 years, how would you live your life differently?
5. If you could ask one person, alive or dead, only one question, who would you ask and what would you ask?
6. If you could live forever, would you want to? Why?
7. If you had to move 3000 miles away, what one thing would you miss the most?
8. If you had to teach something, what would you teach?
9. Is stealing to feed a starving child wrong?
10. What would you not give up for $10,000,000 in cash?
11. Would you break the law to save a loved one?
12. Would you ever give up your life to save someone else?

Would you rather

1. Would you rather be a worried genius or a joyful simpleton?
2. Would you rather lose all of your old memories or never be able to make new ones?
3. Would you rather your child be less attractive and extremely intelligent or extremely attractive and dim?