145 Best Conversation Starters to Skip the Small Talk

How to use this list—quick tips

1. Start with a light touch, then gradually get more intense.Start with a fun question to get things going,and then move on to the more serious topics if the other person seems comfortable.

2. Ask questions that don't have a "yes" or "no" answer.Avoid using yes/no questions.After that, you could ask, "Why?" or "Tell me more."

3. Watch for comfort signals.If the answers are short or the body language is closed off, move on to a lighter topic.

4. Share this too.Turn your answers into conversation by sharing a short story. This helps to build a connection.

5. Try using a range of media.Turn your favourite prompts into image cards, short videos, or shared journal prompts on TellSomething to make conversations more visual and repeatable.

The list — categorized & numbered (145 total)

Fun Starters to Warm Up (1–20)

1. If you could swap lives with any fictional character for a day, who would it be and why?

2. What's the weirdest food combination you love but don't dare tell anyone?

3. If our friend group had a theme song, what would it be?

4. What's the most spontaneous thing you've ever done?

5. If you could relive one day of your life over and over again, which day would you choose?

6. Which TV show that you know you shouldn't watch do you keep watching?

7. If you could instantly become an expert in one skill, which would it be?

8. What song always makes you happy?

9. If you had to choose, which everyday task would you be best at?

10. If you could only eat one type of food forever, which would it be?

11. What's the funniest autocorrect mistake you've ever seen?

12. Plan the perfect holiday — where are we going and what are we doing?

13. What's the best compliment you've ever received?

14. If you had an entrance song, which song would it be?

15. If you could pick any animal (real or imaginary) as a pet, what would you choose?

16. What's your favourite karaoke song?

17. If you could be best friends with any celebrity, who would it be?

18. What's one random fact you love to tell people?

19. If we started a business together, what would it be?

20. What's the silliest fashion trend you ever followed?

Deep Conversation Starters (21–55)

1. What experience, if you had just one, changed how you see the world?

2. What does success mean to you?

3. What skill are you working on improving at the moment?

4. Tell me about a time that you will always remember.

5. How do you deal with failure?

6. What would you change if you could go back?

7. What are you most afraid of?

8. If money didn't matter, what would you spend your time doing?

9. What kind of person would you like people to remember you as?

10. What was the most difficult lesson you've learned?

11. What is the most important thing for you in a friendship?

12. If you had one year left to live, how would you spend it?

13. Do you think people can really change?Why or why not?

14. What are you trying to change in your behaviour?

15. What's the kindest thing someone has ever done for you?

16. Have you ever had something happen that you couldn't explain?

17. What makes you keep going when things get hard?

18. What does your happiest life look like? Can you picture it in one image?

19. What's the biggest risk you've ever taken?

20. How do you measure your personal growth?

21. If you had lots of free time, what hobby would you like to try?

22. What do you think is your best quality?

23. How do you deal with disagreements?

24. When was the last time you made a big decision and felt totally sure about it?

25. What is one thing you have always wanted to do but not yet done?

26. How do you know when you can trust someone?

27. What did you used to believe that you no longer believe?

28. Do you believe in fate, free will, or a combination of both?

29. What's your primary love language?

30. Do you believe in soulmates?Why or why not?

31. Is lying ever okay?When?

32. If you could say sorry to someone from your past, who would it be?

33. What was the hardest decision you ever had to make?

34. What makes your life meaningful right now?

35. What are you most proud of?

Silly & Playful Starters (56–80)

1. What's the weirdest Google search you've ever done?

2. What was the most ridiculous argument you ever had?

3. What's the worst haircut you've ever had?

4. If you had to survive a zombie apocalypse with three celebrities, who would you pick?

5. What's the funniest lyric you sing that you've got the wrong end of the stick?

6. If your pet could talk, what would it say about you?

7. What's the most embarrassing public moment you can laugh about now?

8. What word do you always pronounce wrong?

9. What was the worst text you've accidentally sent?

10. If you had to wear the same Halloween costume every day for a year, what would it be?

11. What talent do you have that nobody knows about?

12. If your life were a sitcom, what would it be called?

13. What is the funniest joke you know?

14. If you could be a cartoon character for a day, who would you like to be?

15. What was the strangest thing you've ever done on a whim?

16. If you could give yourself a silly name, what would it be?

17. What silly prank would you put in a movie montage?

18. If fruit could talk, which would be the funniest?

19. What's the funniest gift you ever received?

20. Which kitchen tool would you choose as your superhero weapon?

21. What's the most ridiculous thing you'd ban if you had the power?

22. Would you rather sneeze confetti or hiccup bubbles?

23. Which of the foods from stories would you like to try in real life?

24. If you could invent one holiday, what would it celebrate?

25. What's a fun fact that makes you smile?

Conversation Starters with a Crush (81–105)

1. What was the worst date you've ever had?

2. What does your perfect lazy Sunday look like?

3. What's the worst pick-up line you've heard or used?

4. What do you like about them?

5. Who was your first crush?

6. What does your name mean? (Or how did you get it?)

7. If your friends were to describe you in three words, how would they say it?

8. What small gesture can make someone instantly more attractive?

9. If you planned the perfect first date, what would we do?

10. What would be the one experience you would love to have with the right partner?

11. If we spent a day without phones, what would we do?

12. If I were a character in a story, who would I be?

13. What song makes you think of someone you like?

14. What do people rarely compliment you on that you want more of?

15. Which movie couple would we be?

16. If I dared you to send me your last screenshot, would you?

17. What's one thing about me that makes you curious?

18. What could we wear as a couple for Halloween?

19. If we got lost on purpose, where would we end up?

20. What would you like us to try together for the first time?

21. What's an unexpectedly fun thing you'd compete with me on?

22. What's your spicy Never Have I Ever (tame or bold)?

23. What's the most romantic small thing someone can do?

24. What would you like to learn from me?

Quick “Never-Fail” Questions (perfect for small groups) (106–120)

1. What was your favourite childhood game?

2. Which film always makes you cry?

3. What's the best meal you've ever eaten?

4. What's a small thing you do every day that makes you happy?

5. What's your favourite way to relax?

6. What would you do if you had a free afternoon?

7. What's the best free thing to do in your city?

8. What do you collect, if anything?

9. What book would you suggest for everyone?

10. What's the most beautiful place you've ever seen?

11. What skills do you wish you had learned earlier?

12. Do you prefer sunrise or sunset?

13. What's your favourite holiday tradition?

14. What makes you happy?

15. Who is one person you really look up to and why?

Conversation Starters for Work or Networking (121–130)

1. What's the most interesting project you've worked on recently?

2. Which skill helped you the most in your career?

3. What professional goal are you excited about?

4. How do you stay focused during long workdays?

5. Have you found any book or podcast that has helped you in your work life?

6. What would you say is the most important thing you learned when you first started working in your field?

7. If you could design your dream job, what would it look like?

8. What career advice have you been given that has helped you?

9. What is the most important thing you do to get yourself ready for work?

10. Who has been your most memorable mentor?

Closing / Getting Deeper (131–145)

1. What recent experience made you rethink something?

2. What small thing are you grateful for today?

3. Which relationship habit do you value most?

4. What memory do you want to keep forever?

5. What's the best compliment you could receive now?

6. What's one boundary you've learned to set for yourself?

7. What are your top tips for looking after yourself when you're having a tough time?

8. What would you like to be remembered for? Even something small would be great.

9. If you could give your younger self one tip, what would it be?

10. What question do you wish people would ask you more often?

11. What is one moment in your life that you would like to relive?

12. What have you done that you didn't expect?

13. What would you like to be written on the front page of your life story?(Metaphorically.)

14. How do you know when you're truly content?

15. What would you like to talk about with someone you love but haven't yet met?

Authority & evidence suggestions

• The Gottman Institute is a place where people do research on conversation, closeness, and relationship-building.

• American Psychological Association (articles on active listening and well-being).

• Harvard Health Blog or Harvard Business Review (articles on how to communicate in a meaningful way and the mental health benefits of doing so).

• A great resource for learning interpersonal skills (for example, Brené Brown, or books on being vulnerable and making connections).

Final

• Make a set of conversation cards (one question per image + picture) for Instagram or Stories.

• Make a short video pack for TikTok or Reels (with suggestions for voiceover and B-roll).

• Make an interactive, private conversation journal so two people can answer and save responses (great for couples or friends).