Conversation Starters

In this article, we’d like to share with you some interesting conversation starters. You’ll also get some conversation starters for networking, casual ones, funny ones, as well as those which can inspire deep conversations.

We have all been in those situations when starting a meaningful discussion is challenging. You are meeting all these new and different people and each time you need to get them talking.

Here, we offer some hints and tips for starting those conversations that end in friendship or end in a fruitful business connection.

Networking Conversation Starters

Networking is a minefield for the shy and the awkward. It can even be a challenge for those who feel comfortable and confident in work-based conversations. Here are some starters to help you get your foot in the door.

  • How did you hear about this event?
  • What company do you represent?
  • Would you recommend somewhere near to eat?
  • What inspired you to get into this line of work?
  • What is the best experience you have had working in this field?
  • Are there other conferences like this you have been to?
  • What would you like your legacy to be?
  • How do think you could take your career to the next level?
  • Who would you love to meet in an elevator?
  • What routine really gets you going in the morning?
  • What goals have you set yourself this year?
  • Did you ever have a teacher or mentor that helped to change your life?
  • Who is the greatest influence in your life?
  • Are there any motivational speakers in our field I should be aware of?
  • Who supports you in your decision-making at work?
  • If you could go back and give your young self some career advice, what would it be?
  • What’s the worst piece of advice you have ever been given at work?
  • What would go back to school to study if you could?
  • I’ve read that (insert business news story here), what do you think?
  • What do you value in life?
  • What is the biggest challenge you face in your career?
  • Do you see any exciting opportunities in your business that you’d like to pursue more?
  • What is the most important event you have attended?

Casual Conversation Starters With Strangers

The best way to get good at conversations is to take the time to practice conversing with strangers. There are lots of ways to stimulate a chat with someone you meet randomly. Here are a few to get you started.

Start Conversations With Strangers
  • How is work going?
  • What’s your story?
  • How do you know the host of the party/ the people you are with?
  • What brings you here?
  • Have you been here before?
  • What has been your high-point today?
  • What has been the highlight of your week?
  • Do you like that piece of art/ drink/ food?
  • Do you know any good restaurants around here?
  • What did you think about that sporting event at the weekend? (specify the event)
  • What do you think about the event that has just happened in the news? (specify the news story)
  • Would you recommend something from the menu?
  • What a wonderful place – do you know anything about where we are?
  • Did you see a certain video or television programme? (specify the viral video or TV programme)
  • Has this been a busy time for you too?
  • Do you come here regularly?
  • Are you going away somewhere nice?
  • What did you do at the weekend?
  • Are you working on any interesting projects?
  • Are you doing anything interesting after this?
  • Having fun? Glad the week is over?
  • Where you get your shoes? (Or choose another item of clothing/ accessory)
  • Can you recommend a place around here to visit?
  • I am grabbing a coffee – could I get you one too?

Funny Conversation Starters

Funny Conversation Starters

Sometimes you just want to be funny – you want to start that conversation that will bond with another through humor. Although the hardest of conversation starters, if successful, humor can work to form bonds quicker than most other approaches. Here are a few funny conversation starters to get you started.

  • What would be your plan during a Zombie Apocalypse?
  • What is the worst fashion disaster you have seen?
  • If you were to join the circus – what would you do?
  • If you could time travel, what would you introduce to the past?
  • What is your most embarrassing story to date? (Don’t take this too seriously. And if you ask it, be ready to share something embarrassing, too!)
  • What is your worst first date story ever?
  • Which famous person would you take into a fight with you?
  • Who would you call to help you bury the body?
  • What job could you imagine your pet doing if they could talk?
  • Who makes you laugh the most?
  • Where is the strangest place you have ever been?
  • What is your worst holiday disaster?
  • If you were only allowed to eat one type of food what would it be?
  • What is your favorite chat up line?
  • Who would you hate to be stuck in an elevator with?
  • Which historical figure would you love to get drunk with?
  • You are allowed 10 minutes to grab anything you want in the mall for free – where do you head to first?
  • Who would play you in a story about your life?
  • What would the reality show about your life be called?
  • What animal would you be if you could?
  • If you could go back in time to a period of history, which one would it be?
  • What is the funniest joke you have heard?
  • If you had to go back in time and change your first name, what would it be? How about your last name?
  • What’s your first purchase after a lottery jackpot win?

Interesting Conversation Starters

Have you ever found yourself in an awkward situation? You know the one where you stand, or sit, face to face with a friend or colleague in a social setting and neither of you seems to have a clue what to say. You’re not alone.

Many people find themselves in these blank conversation moments, especially when they’re meeting each other for the first time or after a long period of separation.

Here are some creative and interesting conversation starters that can save the day the next time you find yourself in a conversation rut.

1. What do you do for fun?

Almost everyone has something they enjoy doing whether it is a hobby or routine chore. Use this opportunity to compare what you like doing with the other person’s response.

2. If you had to choose one thing to take with you to an isolated island what would it be?

The thought of being alone on an island should trigger some pretty creative ideas about how to survive and make for a good discussion.

3. What was your favorite childhood toy?

A nostalgic conversation starter like this could fire off a pretty good discussion on positive childhood experiences.

4. Which subject/class did you enjoy most in high school?

You could follow up this question by asking why this subject/class was so enjoyable or what the person liked about it.

5. Which subject/class did you dislike most during high school?

This is a question that pretty much everyone can answer…in detail. After all we’ve all had that one class, or teacher, that we just can’t stand or handle.

Conversation About Friendship

6. How did you meet your best/closest friend?

This is another nostalgic question. Be prepared though to have your emotions activated as some best friend encounter stories are quite emotional.

7. How far would you go to get a taste of your favorite food?

Food is always an interesting conversation topic. This question should produce some interesting answers as you explore the lengths to which people will go to get a taste of something they love.

8. What do you think about mankind’s reliance on technology today.

Let’s face it. Technology is a big part of life in today’s world. Talking about whether our reliance on technology is healthy or unhealthy can be a good way to explore the issue.

9. How good are you at keeping secrets?

The answer here is either one extreme or the next. You’ll discover whether the person you’re conversing with is a great secret keeper or a poor one… and there are advantages to each!

10. What would you consider to be the perfect gift?

Ensure that you start off with a disclaimer that you are not making a commitment to buy a gift for the other person. That aside, this question is ideal for exploring your preferences.

You can add your ideal gift to the conversation and discuss the merits of each. And if this conversation sparks a long term friendship, you have a head start for gift buying when special occasions arise.

11. What do you believe is the most remarkable/coolest thing about our generation?

Each young generation gets a bad rap for so many reasons it can be helpful to focus on the positives for once.

12. Do you think you could survive in a world without technology?

Another variation of this one could be ‘how do you think you’d handle living in a world without technology?’

13. What is your dream job?

A person’s dream job says a lot about him/her. Exploring this question can result in you learning a lot more about the next person’s ambitions.

14. What’s your favorite hangout/chill spot?

This should be an easy question for anyone to answer. A great follow up question would be ‘why is this your favorite place?’ But if the person you’re conversing with is really interested in the discussion you won’t have to pose this follow-up question.

Chill Spot As A Conversation Topic

15. Of all the things you own which one is most useful?

The person you’re conversing with is bound to own a few things. Through this question you can learn about the value place don one item and to extend the conversation you can share yours as well.

16. How would you describe your fashion style/brand?

Whether it’s quirky, sophisticated, casual or mixed, we all have a fashion brand. Have fun discussing this one.

17. How do you feel about Climate Change?

Climate change is a topical issue, but it does make for a more serious discussion so gauge the situation well before posing this one. Nonetheless the question presents a good opportunity to explore what you and the other individual think about this global issue.

18. If you had the chance to do one thing you never did in high school, what would it be?

Another nostalgic question here. While it focuses on missed opportunities, it can also lead to a revisiting of priorities and a discussion on how the missed opportunity can be

19. If you had the chance to undo one thing you did in high school, what would it be?

We all have regrets and this question encourages reflection on one decision or action that you wish you hadn’t taken. It may also be an opportunity to explore how differently life would have been if that decision or action had not been taken.

20. How many best friends have you had?

It doesn’t matter if it’s one or twenty, this question is sure to spark conversation about close friendships and why they last/do not last.

21. How do you feel about the millennial stereotype?

The millennial stereotype (lazy people who want to reap success the easy way) has been attached to many people… even those who don’t fall into the millennial category.

Use this question to find out what the other person thinks about the stereotype and the related experiences they’ve had.

22. Name one thing that you pay for that you think should be free?

This one will encourage a bit of thinking. Once it is answered, the follow up conversation can be focused on why the selected item was chosen.

23. If you could get a break from one bill which would it be?

We all dream of that bill break so it can’t hurt to explore the possibility in conversation. On a humorous note, you may need to add a disclaimer that you’re not making a bill payment offer before or after asking the question.

Talk About Money Matters

24. Who’s your favorite pop star/celebrity?

This one should provide some insight into preferences and trigger further exploration into entertainment

25. Who would you say has influenced your life decisions the most?

We all have influential figures in our lives. Identifying the most prominent ones and exploring why they had such a big impact could make for an interesting exchange.

26. If you could spend a day with a celebrity who would you choose?

This is an exciting idea to think about which should make the discussion intriguing.

27. What’s your most interesting talent?

This should help you learn more about each other and if the talent turns out to be strange or unique then the conversation will have added appeal.

28. How adventurous are you?

Whether you fall in the extremely adventurous or 0% adventurous group, this question can be the base for a healthy discussion.

29. If you woke up tomorrow as a billionaire what would you do?

This is another exciting conversation starter that encourages you to consider how you’d handle your hypothetical wealth.

30. What’s your favorite sport?

Even non-sports enthusiasts can answer this question

31. What’s your favorite game?

Board games, computer games, team games, card games and others are in the mix for this question. Feel free to explore the reasons for choosing a game.

32. If you could choose a superpower to have for the rest of your life, which one would it be?

You could take this conversation to the next level by choosing an opposing superpower and discussing which would be superior.

33. Which social media platform do you prefer?

This one is a great conversation springboard for today’s young adults. With the many different social media platforms available each offering different features and advantages, you’ll no doubt have an interesting discussion.

34. Of all the movies you’ve watched which one has affected you the most?

Some movies are quite inspirational, informative or even life changing. This question allows you to discuss those movies and the impact they’ve had on your lives.

35. Of all the movies you’ve watched which one was the most disappointing?

You may find out that a movie you found interesting is totally disappointing to someone else. Even so, this is a great way to kick off some discussion.

Start Conversations By Talking About Movies

36. Of all the movies you’ve watched which one did you hate the most?

Follow up this question by asking why the movie is so hated by the next person. You could also share your most hated movie and reasons for detesting it.

37. If you could choose a theme song for your life which one would it be?

An interesting way to spark a discussion on general life issues.

38. If you could migrate to another country which would it be?

Migration to another country can seem to be a whimsical topic but should inspire some interesting discussion.

39. How do you feel about the stereotypes applied to our generation?

This question should stir up some passionate discussion as each generation suffers from labels that are applied to them.

40. What’s the most ridiculous thing you’ve done?

We all have that story about something strange we’ve done.

41. What’s the most ridiculous thing you believed when you were a child?

Of course this one is sure to inspire some laughter as your reflect on how gullible you were as a child.

42. Which food do you hate?

You can’t go wrong with a food-related conversation starter. Expand this one with reasons for disliking the food mentioned.

43. If you could relive one day in your life, which would it be?

We’ve all had a day when everything seems to be going superbly well. Use this as a springboard for a light and positive conversation about that day.

44. If you could shapeshift into an animal, which animal would you choose?

Here is another opportunity for a spirited discussion. After hearing what the other person would choose, you could come up with your own choice and then have fun arguing about which would be better.

45. If you had the opportunity to solve one of the world’s greatest problems which one would you pick?

This question will spark a discussion with a more serious tone, but it will be a healthy discussion in which both participants explore their opinions and concerns about the planet’s biggest problems.

46. Have you ever pranked someone or been pranked? What was the experience like?

Pranks are always easier to discuss after the fact, especially if you were the ‘prankee’, but tread lightly with this one as some people may hold grudges for years after a prank

47. Do you believe in aliens?


The alien controversy (think Roswell) has believers and non-believers and whichever side you select, you can have a grand time justifying your stance.

48. Would you volunteer to be among the first human colonists on another planet?

With discussions in the media surrounding plans to establish human colonies in space supported by great minds like Stephen Hawking, this one is sure to inspire some deep thought.

49. Which method of travelling do you prefer (driving, flying etc)

Travelling is an unavoidable part of life in the modern world, therefore it makes for a good discussion point. Both members of the discussion are bound to have their preferences and reasons for selecting them.

50. What food do you find it hard to avoid even though it isn’t good for you.

Let’s face it even people with severe allergies sometimes find it tempting to taste foods that could trigger illness. This is a great opportunity to find out about the other person’s will power and cravings while sharing a snapshot into yours as well.

51. If you could be reincarnated as an animal, which one would you choose.

A hypothetical situation similar to the shapeshifting one, but this time you’ll be spending a lifetime in the body of an animal so more serious thought is required. Have fun discussing why one animal is a better option than the other.

The next time you find yourself at a loss for words, try a few of these interesting conversation starters. They should be able to help you to spark some interesting discussions and who knows, this may lead to the formation of amicable relationships over time.

Deep Conversation Starters

Sometimes, just sometimes, you really want to get to know someone and get into a long and meaningful chat. But where do you begin? Here we offer a series of deep conversation starters you could ask that could prompt a meaningful discussion.

Deep Conversation Starters
  • What could we do with adding to the world?
  • Are you are a person who likes to stand out or fit in?
  • What has made you curious recently?
  • Name a person you love the most in the world – do they know?
  • What would you tell yourself on your first day on the planet?
  • Do you have a five-year plan? Care to share the broad strokes?
  • What do you think is your greatest strength and your greatest weakness?
  • If you had the freedom to choose – where would you choose to wake up tomorrow?
  • Think back to the first time you feel like you achieved something – when was this and what happened?
  • What event has had the most impact on your life?
  • When was the last time you were so engrossed in an activity that time had no meaning?
  • What was the last major turning point in your life and what happened?
  • If you were allowed to really answer the question ‘how are you?’ what could you say?
  • Where do you find beauty in the world?
  • If you had the chance to speak to yourself five years ago – what would you say?
  • What takes up too much of your time?
  • Describe a time when you have been completely spontaneous.
  • What essential lesson should be taught to every child at school?
  • Who do you miss the most?
  • What do you dream of doing in the future?
  • Name a person you would completely trust with your life?
  • What makes you want to get out of bed in the morning?
  • Feeling any gratitude lately? Have you stopped and smelled the roses?
  • What makes you want to start a fight?
  • What do you value that you could never place a price on?
  • If you had the chance to manipulate time, what choices would you make?
  • What keeps you going in the face of problems and challenges?
  • What’s your passion?
  • Did you abandon any of your passions that you wish you could go back to?
  • What do people always seem to get wrong about you?
  • What information would you choose to un-know?
  • Name the kindest act someone has done for you.
People Talking At Dinner
  • What was the last lie you told and why did you tell the lie?
  • Why do you continue to work each day?
  • If you could never die – how would this change the way you lived?
  • What do you notice first when you meet someone?
  • If you could give a summary of who you are, what would it be?
  • What motivates you each day?
  • What would be your version of paradise?
  • When was the last time you did something for the first time?
  • What habit would you love to develop?
  • Where would you go in the world if you had to stay there forever?
  • Why should you feel grateful?
  • What are your values in life?
  • What do you value in your friends?
  • If you had all the money you could ever want how would it change how you lived?
  • What single event strengthened your belief in the human race?
  • What small things do you appreciate?
  • Which things matter most in life, in your opinion?
  • Would you want your children to turn out like you?
  • What is the closest to death you have ever been?
  • If you ran back into your burning house for one item, what would it be?
  • What weird thing does your family do?
  • If you met a fortune-teller who could really tell the future what would be your one question?
  • What do you wish you could show people about you?
  • What is your motive for living each day?
  • When was the last time you did something new?
  • What upcoming event is giving you hope for the future?
  • What do we need more of in the world?
  • Which personality traits do you find most attractive in a person? (…and how can people who are beautiful on the inside, show it more on the outside?)
  • If you had the chance to give one message to the whole world what would you say?
  • What one thing do you need to do before you die to make your life meaningful?
  • How do you demonstrate your love to your friends and family?
  • What would you love to spend more time doing?
  • Sum yourself up in 15 words.
  • If you could really know about one thing – what would it be?
  • What would you do if you were in charge of your own country?
  • Who do you admire the most and why?
  • If nobody was watching – what would you choose to do?
  • Which year of your life have you enjoyed the most?
  • What do you love and hate about birthdays?
  • How are you choosing to make a difference?
  • If someone was to buy you a gift – what would be a great choice?
  • What makes the hairs on your arm prickle?
  • If you could meet your hero – what question would you ask them?
  • What would you love to finish one day?
  • What single thing or person could you never live without?
  • This of your perfect day. What would it look like?
  • What do you need to achieve today?
  • When do you feel most at peace?
  • If you were to describe success – what would it look like?
  • What is one thing that could happen today to make it even better?
  • Who gave you your favourite compliment and what did they say?
  • What have you learnt to do in the last year?
  • Who would you want to see if you had only 24 hours to live?
  • What was your first thought when you woke this morning?
  • We all have bad habits, what’s your worst one? (Make sure to share yours, too if you can. Showing vulnerability makes you more relatable, and help others consider you as a friend.)
  • What did you want to be when you were a child and how has this changed?
  • Describe a recurring dream.

Time To Act !

We hope these conversation starters have given you more than a few ideas on how to start your next conversations. We recommend you bookmark it if you can. In any case, make sure you apply these conversation starters as soon as possible.

The sooner you take action, the better you’ll internalize these new ideas and improve your conversation skills.

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