101 Conversation Starters For Deep, Interesting & Fun People

Life is too short to be boring; when you start a conversation, start it with a bang.

Our curated list of original, deep, interesting, and funny conversation starters features topics that capture attention and build relationships. Gone are the boring cliche topics, and in with the fun conversations.

Life is too short to be boring; when you start a conversation, start it with a bang.

We will start with hilarious quick-fire conversation starters that are unique and guaranteed a cheeky response. Then we will move on to deeper, more interesting questions that let you inside someone’s deepest thoughts.

Conversation Starters For Deep, Interesting & Fun People
Conversation Starters For Deep, Interesting & Fun People

Good Conversation Topics

Good conversation topics capture the human imagination, focusing on aspirations, dreams, beliefs, and personal experiences.

No great conversation starts with you talking about yourself; they start with you showing interest by asking someone a question about themselves.

When building a list of conversation topics, one quickly realizes there are so many dull topics that make people switch off and start looking around the room for someone else to talk to.

Never say to someone, “Tell me about yourself?”, “Who will win the next election?”, “What do you do for a living?” or “What are your life goals?”; these questions are just too robotic and boring.

Let’s start with funny conversation starters and move on to the deep and meaningful questions of life.

21 Quick-fire hilarious things to talk about

These witty and cheeky questions will ignite a quick laugh response giving plenty of opportunities to discuss the answers. If you are stuck for something to say, fire one of these topics out there.

  1. Tea, coffee, or whiskey in the morning?
  2. In what situation is a fart not funny?
  3. Horror, comedy, or adult movies? Or horrifically funny adult movies? (Cheeky)
  4. Blondes, Brunettes, or bald heads?
  5. Math or history, or choose life?
  6. Do you prefer to be indoors, outdoors, or locked up in a panic room?
  7. City, beach, mountain, or remote jungle cannibal tribe vacation?
  8. Starters, desert, or (heaven forbid) fasting?
  9. Books, audiobooks, or are you 12 and like comic books?
  10. Asian, Italian, or “given up on life” ready meals?
  11. Fruit, Vegetables, or Belgian chocolate and tears?
  12. YouTube, Netflix or do you need a VPN?
  13. Fiction, non-fiction, or “god give me the will to live” self-improvement books?
  14. Are you a serious morning person, a party animal night person?
  15. What are you made from, sugar, spice, or all things nice?
  16. What are you made from, slugs, snails, or puppy dog tails?
  17. What gets you motivated, the carrot, the stick, or a carrot on a stick?
  18. What’s your least favorite color?
  19. What is the dumbest sport on the planet?
  20. What’s your favorite foreign swear word?
  21. Are you a dog, cat, or donkey person?

27 Fun Conversation Starters

These fun conversation starters give your audience the perfect opportunity to say something funny, witty, or quirky that will start an excellent conversation.

  1. What is worse, belching at the dinner table or popping a fart out?
  2. Do you think farts are inherently funny?
  3. What is the worst superhero power you can imagine?
  4. What’s the weirdest thing you’ve ever eaten?
  5. When did you feel the most gangster moment of your life?
  6. What’s the worst gift you’ve ever received?
  7. If you could have any superpower, what would it be?
  8. If you had to have a tattoo to save your life, what would it be, and where?
  9. Are you more hippie, rocker, or wealthy industrialist?
  10. Would you choose immortality or unbridled sexual attraction?
  11. If money was no object, how much would you give me now?
  12. Would you rather be an eagle, a lion, or a dolphin?
  13. What’s the most embarrassing thing you’ve ever seen happen to someone else?
  14. What’s the funniest/worst joke you’ve ever heard?
  15. Which is the best movie, The Godfather or Something About Mary?
  16. Invisibility or the ability to fly?
  17. Describe yourself using an animal sound and movement.
  18. What’s the most embarrassing thing that’s ever happened to you?
  19. What’s your spirit animal?
  20. What’s your favorite comic book?
  21. Who is your favorite superhero?
  22. What is your favorite song of all time?
  23. What was the first music album you bought with your own money?
  24. What is your favorite movie of all time?
  25. Do you believe in UFOs?
  26. Toilet Roll, facing in or out?
  27. What is the longest word you know?

15 Deep Conversation Starters

Deep conversation starters will give you instantly a unique insight into how someone thinks. The answer they provide will cut straight to the fabric of their beliefs and passions.

  1. What’s the best piece of advice you’ve ever received?
  2. If you could go back in time and relive any moment in your life, what would it be?
  3. If you could travel back in time, what advice would you give yourself?
  4. Do you believe in fate or free will?
  5. If you could meet anyone, living or dead, who would it be?
  6. What things make you feel happiest?
  7. Do you think extraterrestrial life exists? If so, where do you think it is?
  8. What do you think happens after we die?
  9. If money was no object, what would you do with your life?
  10. What do you think the meaning of life is?
  11. Do you think people can change, or are they fundamentally the same throughout their lives?
  12. How do you think our world will end?
  13. Do you think people are influenced more by nature or nurture?
  14. What’s your favorite quote?
  15. What would you do with a time machine?
  16. How do you think the universe began?

20 Interesting Questions to Start a Conversation

These easygoing yet interesting questions will start a lighthearted conversation that will let you get to know a person but enables a quick exit if they are boring.

  1. Do you like to travel? What kind of vacations do you like best?
  2. If you could trade places with anyone in the world, who would it be?
  3. Have you ever had a dream that came true?
  4. How would you describe yourself in three words?
  5. If you could have one wish, what would it be?
  6. What are some of your hobbies or interests?
  7. Do you like to plan or go with the flow?
  8. What is the first word that pops into your head?
  9. What’s the weirdest thing that’s ever happened to you?
  10. When you’re feeling down, what do you like to do to make yourself feel better?
  11. Are there any unsolved mysteries that interest you?
  12. Do you believe in ghosts? Have you ever had a paranormal experience?
  13. If you could have any job in the world, what would it be?
  14. If you could be any fictional character, who would you be?
  15. What soul food makes you feel happy?
  16. What’s your favorite word or phrase?
  17. What is at the top of your bucket list?
  18. Are you a morning person or a night person?
  19. Who is your role model?
  20. Do you prefer books, audiobooks, or podcasts?

Conversation Starters Summary

I hope these conversation starters inspire you, make you laugh, and motivate you. Feeling confident, talking to new people, making new friends, or a least making people laugh costs nothing in life, so go out there and enjoy.

Did you try any of these? How did it work out? Let me know in the comments below. 

Barry D. Moore
Barry's 25 years of experience with Silicon Valley Corporations such as IBM, Compaq, Hewlett Packard, Hewlett Packard Enterprise & DXC Technology enables him to share his knowledge of succeeding in today's professional corporate environments and develop a great work life for yourself.