250+ Conversation Starters

The ability to start and hold conversations is one that millions around the world wish to possess. Perhaps you are going on a date with someone that you barely know, or you are meeting with a group of people for the first time. The success of your meeting might largely depend on how successfully you can hold their attention. In this post, I will be showing some of the best conversation starters that I have used; with a large degree of success.

You can use these conversation starters to know more about your date: it can even be used as a game with friends, with each person asking another these probing questions. Without further ado, here are 250+ conversation starters for anyone looking to hold an enjoyable conversation.

These conversation starters are divided into sections; from starters for any situation, to questions for someone you just met, to starters for really deep conversations, and so on.

Conversation Starters for Any Situation

  1. Tell me about yourself.
  2. Have you done anything exciting lately?
  3. What made you smile today?
  4. How did you meet the host?
  5. What’s your favorite form of social media?
  6. What was the last good book you read?
  7. Do you listen to any podcasts? Which is your favorite?
  8. What do you think is the best show on Netflix right now?
  9. Have you been on any interesting trips lately?
  10. What do you think has been the best movie of the year so far?
  11. What song do you wish you could put on right now?
  12. Are you a cat person or a dog person?
  13. Do you think you’re an introvert or an extrovert?
  14. If you didn’t have the job you have now, what would you be?
  15. What’s your strangest hidden talent?
  16. What is something people are always surprised to learn about you?
  17. What is the most rewarding part of your career?
  18. Where do you want to be in five years?
  19. What superpower do you wish you could have?
  20. Where would you go on vacation if you had no budget?
  21. If you could travel back in time, what decade would you choose to live in?
  22. What’s the best thing you’ve ever bought off Amazon?
  23. What’s the last concert you went to?
  24. What is one thing you can’t live without?
  25. What’s the strangest dream you’ve had recently?
  26. What is your favorite book of all time?
  27. How many countries have you been to?
  28. What’s your favorite city you’ve visited?
  29. Would you rather travel via plane or boat?
  30. Would you rather be really hot or really cold?
  31. What are your thoughts on the British royal family?
  32. Do you like documentaries? Have you watched any good ones recently?
  33. Who is your favorite celebrity couple ever?
  34. Which celebrity couple do you wish would get back together?
  35. If you could host a talk show, who would you have on first?
  36. What’s your favorite sport?
  37. What sport do you wish you were really good at?
  38. What’s the best holiday?
  39. How did you spend your last birthday?
  40. Do you believe men and women can ever just be friends?

First Time You Meet Someone Conversation Starters

  1. Are you having a good time?
  2. Why did you come tonight?
  3. Was it a pain for you to get here tonight?
  4. I love that shirt/jacket/dress/shoes. Where did you get it?
  5. Wow, it’s so hot/cold in here.
  6. Do you know a lot of people here?
  7. What are you reading right now?
  8. What’s your favorite restaurant around here?
  9. What’s the next exciting event you have coming up?
  10. Doing anything fun this weekend?
  11. Do you have any pets?
  12. What’s one interesting thing about yourself no one really knows?
  13. What do you do for a living?
  14. If you could move anywhere, where would you go?
  15. What was the last movie you saw?
  16. What do you normally do for fun?
  17. What hobby do you wish you had more time for?
  18. If you weren’t here, what would you be doing?
  19. What is your favorite holiday?
  20. Do you have any nicknames?
  21. What’s your biggest pet peeve?
  22. What is your favorite guilty pleasure TV show?
  23. Tell me three fun facts about yourself.
  24. The food looks great. What’s the best thing you’ve had so far?
  25. Have you ever been here before?
  26. What’s the best thing about your job?
  27. Where did you grow up?
  28. Do you like to cook?
  29. What hobby do you wish you were good at?
  30. What song have you had stuck in your head this week?

Conversation Starters for a Deep conversation

  1. Where’s your life headed?
  2. How do you think you will die?
  3. What are the highest and lowest points of your life?
  4. What is holding you back from being the person you want to be?
  5. How have your strengths help you to succeed? How have your faults hindered you?
  6. What are your biggest goals for your life? What progress have you made in attaining them?
  7. Who are you really? Who is behind the mask that you show to the rest of the world?
  8. How would you react if there was irrefutable proof that God doesn’t exist? How about if there was irrefutable proof that God does exist?
  9. Are humans better at creation or destruction?
  10. What are the best and worst parts of human nature?
  11. What aspects of humans have made us a successful species?
  12. What makes people believe absurd conspiracy theories?
  13. What’s something terrifying that we’ve all come to accept as a fact of life?
  14. If you had to sum up the whole human species in 3 words, what would those words be?
  15. What is the best way to explore human nature: psychology, philosophy, or biology?
  16. Is human nature constant, or is it molded by culture? Can human nature be completely changed by culture or society?
  17. Is what we perceive reality or just a construct of our minds? Can our minds correctly interpret reality or is reality subjective?
  18. Is tribalism and people separating themselves into “us” and “them” groups, a learned or genetic trait? Can it be overcome? If so, how?
  19. How does tribalism and creating in groups and out-groups (e.g. race, religion, sport team fans, people with a hobby, etc.) help and hurt society?
  20. If pressing a button meant you received 10 million dollars, but it also killed 5 people somewhere in the world, would you press it? What if it killed only 1 person or killed 20 people? What if the people were people you knew?
  21. Can people with vastly different cultural backgrounds live together peacefully? How?
  22. What does honor mean to you? How important is it to you? Does your culture value honor? What exemplifies honor in your culture?
  23. How important are morals in a healthy society? What are the most important morals for citizens to have?
  24. In the distant past, a person’s life was very similar to their grandparents’ and grandchildren’s lives. How has the rapid pace of technological advancement changed society?
  25. Do people have an obligation to help others or should people be responsible for helping themselves?
  26. What are the most important factors in maintaining a well-functioning society? What does it mean for a society to function well?
  27. What does the ideal life look like?
  28. What does it mean to die well?
  29. Who do you know who is living life to the fullest?
  30. If you were given an envelope with the time and date of your death inside, would you open it?

Conversation Starters When Networking

  1. How did you hear about this event?
  2. What was the first job you ever had?
  3. What’s a good place to eat around here?
  4. What are you reading right now?
  5. How was your commute here?
  6. What fun plans do you have for the weekend?
  7. What cool conferences have you attended?
  8. How long have you been at your current job?
  9. What’s the most fun project you’ve ever worked on?
  10. Did you hear about (insert latest news topic)?
  11. Where do you see yourself in five years?
  12. Have you ever won an award?
  13. How old were you when you had your first job?

Funny Conversation Starters

  1. If you were in a circus, which character would you be?
  2. What is the worst advice you have given?
  3. What is one thing you should never say at a wedding?
  4. What is the worst pickup line you have ever heard?
  5. If you could only store one type of food in your pocket, what would you carry?
  6. What is the worst present you have ever received, and why?
  7. If you were a farm animal, which would you be and why?
  8. Do you ever sing in the shower?

122 What is the worst piece of advice you’ve ever gotten?

  1. What’s the most embarrassing thing that’s happened to you recently?
  2. Tell me about the worst pickup line you’ve ever gotten.
  3. What is your favorite celebrity scandal right now?
  4. What’s the worst thing you’ve ever worn?
  5. If you could do anything illegal without getting in trouble, what would it be?
  6. What is the stupidest joke you’ve ever heard?
  7. When was the last time you laughed so hard you cried?
  8. What’s the best prank you’ve ever played on someone?
  9. What do you think is the funniest movie ever?
  10. What always makes you laugh, even when you’re upset?
  11. Who is your favorite comedian?
  12. What weird conspiracy theory do you believe?
  13. Is a hot dog a sandwich?
  14. Which celebrity would play you in a movie about your life?
  15. What’s the weirdest thing you loved as a child?
  16. What is something that’s really popular right now that will be ridiculous in five years?
  17. What’s the worst trend you’ve ever taken part in?
  18. What’s your go-to joke?
  19. What is the worst first date you have ever been on?
  20. Have you ever stalked someone on social media?
  21. What is the best part about taking a selfie?
  22. What is your favorite celebrity scandal?
  23. If you could do anything illegal without getting caught, what would you do?
  24. What is the weirdest food combination you’ve ever tried?
  25. Did you have an imaginary friend? What was his/her name?
  26. Have you ever had a dream where everyone was in their underwear?
  27. Have you ever been on a blind date?

Conversation Starters For Talking to Kids

  1. If you could make up a school subject, what would it be?
  2. What is your very favorite letter of the alphabet? Why?
  3. If someone gave you 20 dollars, what would you buy with it?
  4. If you had a chance to eat dessert for breakfast every day, what dessert would you choose?
  5. What is the first thing you think about when you wake up in the morning?
  6. Which animal at the zoo do you like best?
  7. If your friend is sad, what do you do to make them feel better?
  8. If you had the opportunity to invent a new ice cream flavor, what would it be?
  9. What is the silliest thing someone has ever said to you?
  10. What’s your idea of a perfect playground?
  11. What’s your favorite word?
  12. Would you switch roles with your parent if you had the chance?
  13. When was the last time you used the words “thank you”?
  14. If you had a robot for the entire day, what would you ask it to do?
  15. Do you prefer cold weather or hot weather?
  16. If you never had to eat one vegetable, which would it be?
  17. What was the last thing that made you smile?
  18. What is your favorite part about school? Your least favorite?
  19. How do you make friends?
  20. Who makes you laugh the most?

Conversation Starters On A First Date

  1. How did you become close with your best friend?
  2. What’s your favorite movie that you could watch over and over again?
  3. What has always been your dream job?
  4. If you could date one celebrity, who would it be?
  5. Are you a spender or a saver?
  6. What do you like most about your job?
  7. What do you think is your most annoying quirk?
  8. What’s the weirdest text message you’ve ever gotten?
  9. What do you hate the most about dating?
  10. Where’s your favorite place in the world?
  11. What’s the best vacation you’ve ever been on?
  12. How close are you with your family?
  13. Do you prefer to stay in or go out?
  14. Where did you go to school?
  15. Have you ever lived anywhere else?
  16. What are you good at that you’re really proud of?
  17. What’s your secret talent?
  18. What do you think is the most annoying habit?
  19. Tell me about one thing on your bucket list.
  20. What do you dislike most about your job?
  21. What are you the most passionate about?
  22. Do you like calling or texting better?
  23. What are your honest thoughts about social media?
  24. What do you look for in a relationship?
  25. Did you hear about (a big news story)?
  26. What is one thing that made you laugh this week?
  27. What’s your favorite food?
  28. What’s the worst thing you’ve ever eaten?
  29. What movie are you really excited to see?
  30. How do you spend your free time?
  31. Are you a morning person or a night owl?

Strange Conversation Starters

  1. If you could be on a different planet tomorrow, which planet would you choose?
  2. Do you think when you die your soul dies too?
  3. If you were going to die tomorrow, what would you do today?
  4. If you could be a superhero which one would you be?
  5. If you had to get stuck in a video game, which one would you choose?
  6. Would you rather be a famous actor or politician?
  7. Would you rather throw up or have a severe stomach ache?
  8. Would you rather be fully heartbroken and ruined for life or never love?
  9. Would you rather die young and happy or old and depressed?
  10. Would you rather be a drug addict or a murderer?
  11. Would you rather be able to fast forward or rewind time?
  12. Would you rather be able to fly or breathe underwater?
  13. Would you rather have the ability to teleport or read minds?

Dinner Party Conversation Starters

  1. When you die, what do you want to be reincarnated as?
  2. What is your favorite guilty pleasure TV show?
  3. What was your worst “foot in mouth” moment?
  4. Who would you swap lives with for a day?
  5. If you could live anywhere in the world, where would it be?
  6. What is the strangest gift you have ever received?
  7. What is the funniest gift you have ever given?
  8. What are three fun facts about yourself?

Conversation Starters For A Family Gathering

  1. What time would you travel to?
  2. What is one thing you can’t live without?
  3. What is your least favorite chore?
  4. What is your earliest memory?
  5. Who are you most thankful for and why?
  6. Where do you want to go on the next family vacation?
  7. What’s the nicest thing a family member has ever done for you?
  8. What was the biggest punishment you’ve ever received?
  9. If you could describe yourself in three words, what would they be?
  10. What would be the first thing you would do if you traded places with your family member?

Conversation Starters At A Bar

  1. What drink do you suggest I get?
  2. How do you get to X place from here?
  3. Where is a good place to get food around here?
  4. I’m NAME, what’s your name?
  5. Are you having a good time?
  6. Batman or Superman, who would win?
  7. This song is so overplayed, I’d rather hear X. How about you?
  8. What’s the worst thing one can say on a first date?
  9. What made you laugh this week?
  10. Are you having a good evening?
  11. What do you think of this place?
  12. Which song would you make you dance at this very moment?
  13. How do you always get a bartender’s attention?
  14. Would you ever dance on top of this bar?
  15. Have you ever done karaoke?
  16. I like your shirt, where did you get that?
  17. How do you know the friends you’re here with?
  18. Do you know so-and-so?
  19. What made you laugh today?


So there you have it: 250+ conversation starters. Use these to have a great conversation with friends and strangers.

Scroll to Top