Dumb Little Man

160 Interesting Questions To Ask To Be An Effective Conversationalist.

Coming up with a good conversation starter is a great way to prepare yourself whether you are at a party talking to someone you have just met, with friends that you haven’t seen in a while or a new lover you are interested in, or your current partner.

In all these, coming up with a conversation starter that isn’t boring can be an enormous struggle. But worry not here is 160 questions to ask To Be An Effective Conversationalist. These questions are meant to make the conversation interesting, insightful, and entertaining.

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It is vital to also understand that what you tell anyone depends on where you are a good example would be what you say to someone depends on where you are. You’re not going to say the same thing to a first date as you would too, say, a child.

And I know it sounds too good to be true, but the right question to ask someone can change your life. It can lead to new relationships and help current ones to grow. Having good questions to ask can also just be a fun way to pass the time. You never know what could happen, and that’s what makes questions so fun.

🕵 Here are some interesting questions to ask that bring a natural conversation to life 🕵

1. What is your favorite season? Why?

What is your favorite season? This is a great conversation starter the reason being it is a question that could probably conjure up some wonderful memories that could spur some wonderful memories.

It is important to have fun as you reminiscence on all the memories linked to your favorite season. It is an interesting question to start a small talk.

2. What is your favorite food/drink.

If you are meeting someone in a bar or restaurant, this is a relevant conversation starter, to begin with. It gives one an idea of what the other party likes and can make a conversation lively as it drives the talk from the food/drinks to other things. Food stirs fun conversations.

3. Where did you go to school?

You have just met a new person and you want to know them better, there isn’t a great conversation starter than asking them where they went to school. This gives you a perspective of what to talk about as the conversation progresses.

4. Do you like to cook?

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Did you know that food is a great conversation starter that not only brings people to discuss a few ideas but might also learn a few new recipes in the process?

5. Could you live without your internet?

We all love the internet and one way of getting another person to speak up is by using this conversation starter. We all know the internet is essential but what would life be without it? Start there and see everything else fall into place.

6. What is your most memorable day?

Humans love talking about their favorite experiences, it is a pure positivity charm that many seek to engage in. Trigger that and keep the conversation going.

7. Do you have a perfect day?

This one is a game-changer because one’s imagination can run wild. Pose the question and delve in to understand what the other person goes through.

Know what a good and bad day looks like, share some ideas in the process and you will find yourselves talking.

8. Lately, have you done anything that is exciting?

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When a conversation is stirring in the right direction, you can ask about things a person has been doing lately. Be it hiking, a charity event, or anything that raises adrenaline, this question can open up a stream of interesting conversation.

9. What social media platform is your favorite and why?

Many people looking for quick laughs will prefer TikTok and IG. People with political interests, business ventures will be on Twitter. Asking what platform someone likes might tell you what they are into.

10. Read any interesting books lately? What genre why they, lessons learned from the books?

Reading books can be a reflection of how someone spends his time. People who read more books are interested in learning new things.

For that reason, asking someone what they are reading lately gives you a window into their private life. Be it romance, science fiction, horror, or fairytales, reading books never gets old. Get to know if one has any fictional character that they love.




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11. Do you listen to any podcast; why do you listen to it?

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Gimlet media brings reply all, a podcast centered towards conventional society. I listen to this podcast as it is vast with knowledge about modern-day society.

If a person listens to sports podcasts, they like sports. Other people enjoy political podcasts or economic podcasts. If you want to engage by asking deep questions, then this is the right type of question to ask.

12. Where do you stream movies from?

In an age where you don’t have to go to the cinema to enjoy a blockbuster, streaming networks like amazon prime and Disney plus are frequently visited by movie lovers.

This is a great question to ask during a conversation as it opens up other questions like what movies or tv shows one enjoys the most. What fictional character do you love, share and engage more?

13. Which is your favorite show on Netflix?

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Every person has one or two favorite shows. Breaking bad and the office is top of my queue. What can I say, I like to get into action and sometimes, just relax and have a great laugh. You could get an interesting answer that may change and attach you more.

14. Have you gone on any trips recently?

Adventure is a thing many desire. Few get to visit places far and beyond due to reasons such as budgetary constraints.

If a person has been on many trips, it shows a free spirit, one of desire and freedom. Trip stories can be intriguing, especially cruise stories. This is one of the fun questions you can ask someone.

15. What is your favorite song?

Musicians never sleep. When one puts a mic down, the other peaks it up. Songs are a great form of entertainment and the most readily available. Ask this question, someone might have read music taste that can be infectious.

16. Are you into any pets?

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People will ask if you are a dog or cat person. I prefer being broad as a person can be in neither. Pets go a long way, not just dogs and cats, but birds and other insects too. If a conversation gets to a place where you both have a mutual love for a certain animal, then it defiantly will be a simple conversation, almost natural.

This isn’t a good question to ask a guy, but it makes you know the kind of person one is.

17. Are you an introvert or an extrovert, reasons?

Socializing freely isn’t a thing for everyone, introverts will tell you. Extroverts will tell you how easy it is to socialize and make friends.

Either way, asking these questions helps you know who the other person is, and with that, you set the tone of your interactions. You can even discuss some personality traits along the way.

18. Is your job what you always wanted, if not, what do you see yourself doing?

Many people are doing jobs for the sole purpose of footing the bills. Ask the other person if what they are doing is what they intended to do. You might be surprised by what you hear.

Get to also ask what their current job is and what motivates them. It is a great question to ask a guy as it gives one an idea of one’s real life.

19. Do you have any hidden talents?

Discovering your talent can be the toughest test you ever have to face. Other people discover that they have hidden talents and every once in a while, they share with people. Someone can be a knife thrower, archer, pigeon racer, or a fire eater Interesting.

You may just learn someone’s favorite board game in the process.

20. What makes people surprised when they meet or interact with you?

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It will surprise you how much there is to learn about a person when they respond to this question. It gives you a tune to know them better and gauge what to engage in or not. It speaks more on the character of individuals.


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21. What is the best part of your career?

It’s good to talk about work and what both of you do in a conversation. After all, if you really want to know a person beyond the surface level you have got to dig deeper, and this is the way to go. Know about their thoughts, goals, and dreams.

You can learn someone’s biggest fear through these and maybe find a way to talk to them and help.

22. Where do you see yourself five years from now?

This question sounds like an interview one but again it is a great conversation starter. It is one of the random questions you can ask anyone. Sharing such personal information strengthens any relationship, and deeper questions focus on that personal self-disclosure.

23. If you were a superhero, what powers would you wish to have?

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Wonderful conversation starter that sets the tune and digs deeper into the conversation. It allows you to get one’s ideas about their deepest imaginations and fantasies. You can use it anytime. It also helps you know what his/her favorite movie is and why.

24. Where is your dream vacation destination?

Everyone loves vacations. We all have our favorite holiday destinations. People want to go to different places all the time. Knowing some places your friends want to go is a great way to get to know them even better.

25. If you had to choose when to be born, which decade would you choose to be born in?

This one is a little more inventive and entertaining. What makes it so is because it is a random question. They may need to think about it for a while before responding, or they may know the answer immediately. Don’t forget to inquire why!

26. Do You Shop Online Often?

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This is a question you would ask someone to know what they love to buy; what kinds of shopping they like to do. It is a good conversation starter if you intend to take such a person online.

27. What Is the Craziest Thing You Ever Bought On Online?

We all shop differently and on different sites and often we don’t get what we ordered. Such a question could get you cracking up. People have bought weird things online.

28. Have you met any celebrities, who?

A chance encounter with a celebrity is always exciting and discussing it with a stranger is a pleasant icebreaker

29. When Was the Last Public Gathering You Attended?

You can use this question to determine if one is an introvert or extrovert.

30. What Are Your Top Five Essential Travel Items

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Sure, you’ll get the standard keys, smartphone, purse/wallet responses, but you might also learn about a unique keepsake or lucky charm that they treasure.

31. What is the weirdest dream you ever had?

Sure, talking about dreams might be boring, but if you’re talking about the craziest dream they’ve EVER had, it could be quite entertaining. Or maybe not. Let’s see what happens!

32. Have you been to any other countries, which?

The answers to this question vary greatly depending on the country you are both from. Are you based in the United States? You may discover that the majority of people have never left the country or have only visited once or twice foreign countries. Is it appropriate to inquire in Europe? You’ll almost certainly receive a slew of travel stories from other countries.

33. What’s the phone app you use most?

You’ll get to know the one they can’t live without, even if it’s not one of their favorites.

34. Would you rather cook or order in?

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I prefer to cook my own meals but this question helps get the moods of a foodie up and open them to talk.

35. Have you ever disliked something and then changed your mind?

36. What’s your favorite board game?

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37. How do you take your coffee?

38. What’s your most prized possession and why?

This is a wonderful general conversation starter, but what’s truly pleasant is getting some thoughts on what works well and is generally awesome to have.

39. Is there any product that you couldn’t live without?

Wine or chocolate? Bread? This question has no bad answers, so it’s another winner.

40. Do you sleep with a top sheet? Why or why not?

41. What is the most annoying habit someone can have?

Find out what annoys them, chances are it probably annoys you too. Then it’s easy to step into a conversation about annoying habits.

42. Where is the most beautiful place you have been?

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This one will probably lead to a good travel story. And conversations about travel are always fun.

43. Where do you spend most of your free time/day?

Find out what their day-to-day looks like. It’ll be easy to start up a conversation about anything of the things they do on the regular.

44. If you could have any exotic animal as a pet, which would it be?

Questions can help deepen any relationship, but you should never have to ask these ones if you’re in a healthy relationship:

45. What is the best city you wish to visit?

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This will allow you to discuss the location you’d like to visit. It’s also a terrific method to see if you have similar travel interests.

46. Do you prefer traveling by train or bus?

This one is likely to vary greatly depending on where you are in the world. However, most people have a favorite that they enjoy discussing.

47. What are your views on climate change?

I’m guessing it depends on where you reside. Many individuals desire what they do not have. So, if you live somewhere with four seasons, I’m guessing you would want to live somewhere with a long summer. But feel free to put my theory to the test with this question!

48. Do you watch documentaries, which?

Perfect for kicking off a lively discussion on the finest and worst documentaries you’ve both seen.

49. Your top three celebrity couples?

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50. Celebrities you wish were dating?




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51. What is that one talk show you love?

Almost certainly, the show they describe will be one you’ve seen and can discuss; if not, you can persuade them to explain what the show is about and what they enjoy about it.

52. What is your favorite sport?

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This could be a list that is very similar to the sports they enjoy watching, or it could be a completely different one. In any case, talking about something the individual is enthusiastic about is a wonderful approach to start a conversation.

53. Do you participate in any sport?

This could be a list that is very similar to the sports they enjoy watching, or it could be a completely different one. Talking about something the individual is enthusiastic about is always an excellent way to strike off a conversation.

54. What is your take on birthdays?

Some people think that it’s superficial to think that the day they were born matters because one day we’ll all die so they prefer celebrating while others may think that it’s just another day as will be tomorrow. This will bring up stories that will keep the conversation going.

55. Do you think the world could be a better place without nuclear?

You can both probably think of ways nuclear power has made the world better or worse at the same time.

56. Can men and women be just friends?

I believe friendship is based on respect and mutual trust and not sexual attraction. But someone else might say if both parties are single it can often develop into something larger. Find out their take and ask why.

57. Are you having a wonderful time?

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Look for someone who is alone but appears to be having a good time as a great cold approach start. It’s simple to sit next to someone at a table or stand next to someone at the bar and just inquire, “Are you having a nice time?” or “Are you having fun?” It’s a nicer way to start a conversation than simply asking, “How are you?”

58. Do you have a favorite restaurant?

This will most likely reveal a lot about their preferred dining establishments.

59. How is college?

60. Have any plans this weekend?

Another inquiry that aims to elicit what they actually enjoy doing is this one. And everyone enjoys discussing topics about which they are enthusiastic.

61. What are your hobbies?

This is an intriguing question because, while it appears easy enough, it gets to the heart of what people genuinely want to do with their time if given the opportunity.

62. What do you do for fun?

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With this one, you can discover a secret talent or a pastime you were unaware of. Both can be the start of a great conversation.

63. Do you have a nickname?

With this one, you’ll have him/her laughing. Sure, it’s a little humiliating, but the stories behind the nickname make for great light-hearted conversation.

64. Any long-term goals?

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Some people are secretive about their own ambitions, while others are outspoken about them. Make sure this isn’t the first question you ask someone. Before popping this one, it’s best to get to know them a little better.

65. Do you have any role models?

You might be able to question an inspiring individual, such as a supervisor, an author, or even a celebrity, about their role model. This is a fantastic method to discuss who inspires you as well!

66. Any regrets in life?

It’s fun to speculate on roads not taken and what may have been. And we all wish our previous selves had done something to help our current selves. Just keep in mind that in 5 years, you’ll be looking back and wishing you’d begun something. The ideal time to plant a tree, as they say, was ten years ago, but the second-best time to plant a tree is now.

67. Your biggest accomplishment?

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This one is fun since they get to brag about their success. Even though they are modest, they probably love having their success acknowledged.

68. Do you have a bucket list?

We all seem to have an ever-expanding to-do list. Discover what’s on theirs Or maybe they’ll go in a new way and chat about unfinished novels, movies, or games.

69. What are you most afraid about?

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It’s strange how anxieties alter as you become older. Some things gradually lose their fear, while others take their place.

70. What is the biggest risk of them all that you took?

Determine how risk-averse they are. Are they willing to take great risks for big rewards, or are they more cautious? Everyone loves a good movie, so why not make it a conversation topic!

71. What’s your favorite genre of movie?

It’s a pretty standard conversation opener, but it’s a wonderful starting point for a talk about their favorite movies

72. What movie scene choked you up the most?

We’ve all had that scene that makes us cry every time. Find out which movies cause them to cry and which cause them to sob uncontrollably.

73. What’s the strangest movie you have ever seen?

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There are some OUTRAGEOUS films out there. I’m sure you’ve seen some, but if you haven’t, you should. Nothing beats a movie that is so odd and bad that it is entertaining on a whole new level.

74. What was the last movie you watched? How was it?

Perhaps you saw it as well, or perhaps you’ll get a fantastic recommendation for a movie you wouldn’t ordinarily consider. Here are some topics for discussion for all you book lovers out there.

75. Do you prefer physical books or ebooks?

They both have advantages and disadvantages, and most people have a clear preference.

76. How often do you go to the library?

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This topic is ideal for kicking off a discussion about how libraries are evolving and your local library. Did you know that some libraries are now lending out tools and cooking materials in addition to books? That’s awesome.

77. What book has influenced you the most?

There is undoubtedly one book that has stayed with them over the years, whether they read it later or a long time ago.

78. What book has changed one of your long-held opinions?

Books have the capacity to mold and transform our perceptions of the world. Typically, for the better.

79. What was the last book you read?

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A good question to find out what kinds of novels people enjoy. And if they like the book, you’ve got a good recommendation. We all have a lot of apps on our phones, so why not talk about them?

80. What’s the most addictive mobile game you have played?

We’ve all been in that situation. Sure, you know you should stop, but it’s just so delicious!


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81. Do you text more or call more? Why?

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While there are exceptions, the answer to this question will be heavily influenced by age. And they’re likely to have strong feelings about their preference, which always makes for a lively discussion. So long as you don’t get into an argument with them.

82. What do you wish your phone could do?

They’re becoming better, but are they getting better in the ways you want them to? What features do you like to see in the next generation of smartphones?

83. What is the most annoying thing about your phone?

Phones have a love-hate relationship. You may now both moan about your phones. Together!

84. Do you experience phantom vibration? (Feeling your phone vibrate even though it didn’t.)

This one is related to obsessive phone checking. However, I believe this is a fairly typical occurrence.

85. Which app has helped society the most? Which one has hurt society the most?

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This one can have an extremely deep discussion regarding technology and society. Or maybe not. It all depends on how the conversation progresses.

In any case, I’m confident you’ll be able to strike up a pleasant conversation with this one. Clothing-related conversation topics are usually popular.

86. Does fashion help society in any way?

This is a bit philosophical, but it may be a fun topic to debate. If the person appears to be interested in deeper conversations, you may try this one.

87. What is the most comfortable piece of clothing you own?

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It could be their favorite t-shirt or some cozy jammies. In any case, there is bound to be something they enjoy resting in.

88. What is the most embarrassing piece of clothing you own?

This is usually a good one because we all have some embarrassing pieces of apparel in our closets that we either secretly adore or haven’t gotten around to getting rid of.

89. What is the best pair of shoes you have ever owned? Why were they so good?

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Comfortable shoes that also look beautiful are hard to come by. You never know you might get some terrific advice on a new pair of boots.

90. Do you care about fashion? What style of clothes do you usually wear?

Some people care a lot about fashion, while others don’t, and still, others care a lot yet pretend not to. Which of them are they? It’s time to enjoy the holidays with some holiday talk!

91. What holidays have been over-commercialized?

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“All of them” is a perfectly valid answer, but this is a nice starting point for discussing the topic in general as well as some of the newer holidays that appear to be coming up.

92. Do you wish there were more or fewer holidays? Why?

So there are a TON of “holidays” to choose from. However, there could always be more, different ones, or fewer. Or, even better, extra vacation days where you can skip work or school. Those are always entertaining.

93. If you had to get rid of a holiday, which would you get rid of? Why?

There are clearly some holidays that may benefit from some pruning, rebranding, or even outright replacement. Columbus Day, I’m looking at you. You can find out which holidays they dislike by asking this question.

94. What is the biggest holiday for your family?

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Whether holidays are normally a massive disaster or not, every family has at least one holiday where they go all out.

95. Does having a day off for a holiday increase or decrease productivity at work?

Sure, you might believe that taking a day off would reduce productivity, but happy employees tend to get more done. So, does it all balance out? You can now both weigh in and make a decision together.

Everyone has to eat, whether they are a foodie or not, which makes it a terrific topic to discuss.

96. What foods do you absolutely hate?

Everyone has foods that they despise. And they usually like discussing why they despise them so much!

97. When was the last time you had a food fight?

What person doesn’t enjoy a good food fight? Anyone who doesn’t want food on their clothes, I suppose… or anyone who dislikes wasting food… They can, however, be entertaining.

98. What do you get every time you go grocery shopping?

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We’ve all got that one snack or goodie that we can’t stop eating. And who knows, by asking this question, you might just discover your new favorite snack.

99. What food do you know you shouldn’t eat but can’t stop yourself?

Don’t be concerned; I believe we all do. And it’s likely that the person you’re speaking with has one as well.

100. Do you like spicy food? Why or why not? What is the spiciest thing you have ever eaten?

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Have you seen any footage of individuals eating hot foods or peppers? Some of those appear excruciatingly painful, especially when they wipe away tears and it gets in their eyes. Ouch!

Casual questions

Casual These questions aren’t overly personal, and they’re perfect for getting to know new people. They can, however, be entertaining to ask someone you already know well.




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101. Are you usually early or late?

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It’s an unusual question, but it’s a good one if you’re going to get to know them and see them again. At the very least, you’ll know when to anticipate them the next time you meet. If they are normally on time and you are usually late, you may want to make an extra effort to be on time.

102. What’s your favorite drink?

It might be alcoholic or nonalcoholic, but everyone appreciates talking about what they are passionate about. And you’ll know what to get them if you ever need to buy them a drink.

103. What’s your dream car?

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Another topic to get them talking about what they like, and who knows, it might be a car you’ve been eyeing, and you can start a conversation about cars.

104. What are you absolutely determined to do?

This one takes a look at some of their dreams or goals and tells you what they regard to be a priority in their lives. And that can lead to some interesting discussions about whatever they want to achieve.

105. What takes up too much of your time?

This will tell you a little bit about what they dislike and, most likely, a little bit about what they would prefer be doing.

106. What’s the best way to start the day?

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This will undoubtedly reveal a lot about their routines, or at the very least the routines they wish they had.

107. What are some things you’ve had to unlearn?

This is a terrific method to learn about the misconceptions or false beliefs they’ve had to overcome.

108. What is special about the place you grew up?

Everywhere has something distinct and special about it. It doesn’t matter if it’s a person, a place, or a thing; I’m sure they have fond memories of where they grew up.

109. What’s worth spending more on to get the best?

This inquiry will get to the heart of what people value most, whether it’s food, clothing, or something else. Or at the very least, offer you an idea of something you may improve in your life.

110. What’s something you like to do the old-fashioned way?

Modern conveniences are wonderful, but sometimes the old ways are the best.

111. How do you relax after a hard day of work?

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What someone does in their spare time frequently reveals more about who they are than what they do for a living.

112. What would be the most amazing adventure to go on?

Everyone has a distinct view of what constitutes an adventure. Some people prefer the extreme, while others prefer the banal. But you’ll soon find out which way the person you’re attempting to get to know leans.

113. What’s the best way a person can spend their time?

This simple question might reveal a great deal about their worldview. The individual may state anything like “helping the underprivileged,” “better oneself,” or “having pleasure.” Whatever their response is, it will help you learn more about who they are.

114. What is the luckiest thing that has happened to you?

While some are lucky than others, we’ve all enjoyed some good fortune. You can now learn about their excellent fortune.

115. When people come to you for help, what do they usually want help with?

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What kinds of difficulties do the person you’re seeking to get to know excel at solving? Tech? Fashion? Cars? Something completely different? It’s time to find out!

116. If all jobs had the same pay and hours, what job would you like to have?

Another inquiry that can assist you to determine what type of work they believe would be best for them. It’s a terrific method to discover what they enjoy doing the most.

117. What is something that most people consider to be a luxury, but you don’t think you could live without?

It could be a distinctive brand. Or maybe some sort of technology. Perhaps something akin to a massage. There are many luxuries that we believe we require.

118. What gets you fired up?

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Different factors motivate different people. It could be a social cause, physical activity, or money.

There are a plethora of possible responses to this one.

119. What do you take for granted?

We are all prone to taking things for granted. It’s a natural element of being human. It can be eye-opening to observe what they believe they take for granted.

120. What’s something you are self-conscious about?

Whether it’s their appearance, the way they speak, their past, or their present, almost everyone is self-conscious of something. And exposing one’s flaws is a terrific way to get to know someone. Just remember to be encouraging.

121. Have you ever given to any charities?

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If they have, you may discover what kind of charities they believe are worthy of donations. And if they haven’t, you know they aren’t the type of person who donates to charities.

122. What was the best compliment you’ve received?

This one is fun since it tells you what accomplishments they are most proud of and provides you an insight into what they think is essential in life.

123. What are you really good at, but kind of embarrassed that you are good at it?

Sharing embarrassing things generally draw people closer, unless it’s extremely upsetting and makes you uncomfortable. But, in general, opening up is good for getting closer; just don’t tease them too much about it or appear too grossed out by it.

124. What’s the most immature thing that you do?

Another question that may encourage the other person to open up a little more and allow you to demonstrate that you are not going to judge them.

125. What are you most likely very wrong about?

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The individual you’re speaking with, like you, undoubtedly has some questions about what they’re doing or even what they believe. And if they don’t, you’ll know they’re the type of person that has no doubts.

126. What is the biggest lesson you NEVER learned?

Another question that can reveal a lot about a person and what they value, or at the very least how obstinate they are.

127. What was the most memorable gift you’ve received?

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There are numerous viable answers to this one. Everything from a kind gift to a childhood gift to a stupidly lavish gift.

128. What chapters would you separate your autobiography into?

This is an excellent question to start a conversation about there and your own histories, and how each of your histories has shaped you into the person you are now.

129. What do you spend the most time thinking about?

This is a great question since it gets to the heart of what the person is most concerned about. It could be a job, a passion, insecurities, or anything else. Whatever their response is, it will reveal a lot about them.

130. What’s the best thing you got from your parents?

It could be something tangible, something monetary, a lesson, or even just genetics. Whatever it is, it might reveal a great deal about what they value and consider significant.

131. What is something you are certain you’ll never experience?

It could be something completely out of character for them, or it could be something they believe will never happen. But, whatever it is, make sure to follow up with a lot of questions about why they chose that one.

132. What’s one responsibility you really wish you didn’t have?

We seem to amass more duties as we become older. With this inquiry, find out which ones they wish they could ignore.

133. In your group of friends, what role do you play?

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Which are you, and which are they? Do you play the part of the planner, the responsible one, the crazy one, the funny one, the quiet one, the smart one, the driver, or do you play a different role? In either case, a person’s role with their friends can reveal a lot about them.

134. What were some of the turning points in your life?

Sometimes life hinges on a seemingly small decision, and other times it hinges on a decision we know will impact our lives forever. Sometimes it’s not our choice at all, but rather life or the people around us surprising us with something that transforms our lives forever.

135. Which of your scars has the best story behind it?

Many scars have an interesting history behind them, and everyone enjoys trading stories!


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136. When people look at you, what do you think they see/think?

I enjoy this question because it allows you to discover a lot about someone by asking them to describe the difference between how they believe the rest of the world perceives them and how they actually are.

137. Which is more important, having a great car or a great house? Why?

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Do they worry more about impressing others or having cool goods for themselves? It’s always useful to know! And you can simply shift into a chat about vehicles or dream mansions that you or they want.

138. If you opened a business, what kind of business would it be?

If the individual you’re talking to is in any way entrepreneurial, this might be a great discussion opener. It’s always interesting to hear and discuss new company concepts. Don’t forget to elicit as many details as possible regarding their ideal business.

139. Who in your life brings you the most joy?

A great question to keep things cheerful, and they’ll be talking about someone they like, so it’ll be easy to start a conversation about who that person is and why they’re so fantastic.

140. What is the most annoying habit someone can have?

Find out what irritates them; chances are, it irritates you as well. Then it’s simple to go into a discussion about unpleasant habits.

141. Where is the most beautiful place near where you live?

This one will most likely result in a good travel story. Conversations about travel are usually entertaining.

142. What is your guilty pleasure?

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Everyone has something they adore, but it may not be in line with how others perceive them or how they perceive themselves.

143. What do you do to get rid of stress?

Everyone experiences stress from time to time, and everyone handles it differently. Learn how they deal with it and perhaps pick up some extra stress-relieving strategies for yourself.

144. What do you think of tattoos? Do you have any?

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If they do have tattoos, each one most likely has a story behind it. And if they don’t have any, it’s still useful to know what they think about them.

145. Where is the worst place you have been stuck for a long time?

We’ve all been in situations when we had to wait for what seemed like an eternity, whether it was at an airport after a car broke down, or for something else. It has an excellent chance of turning into a good story.

146. How often do you stay up past 3 a.m.?

It’s time to find out if they’re a night owl or an early bird! This can easily lead to a discussion on what they prefer to do in their spare time.

147. What do you like to do in the spring?

The arrival of spring is usually a nice time of year, whether trekking or simply resting on the porch.

148. What flavor of ice cream do you wish existed?

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There are so many flavor combinations. I’m craving spicy ice cream. I’m sure it’s out there; I simply haven’t found it yet.

149. What skill would you like to master?

Another inquiry that inquires as to what they are interested in, or what they would like to become interested in.

150. What age do you wish you could permanently be?

This is a nice topic since it elicits some intriguing responses, but it’s also worth noting that the age people choose is usually when they were the happiest. Make careful to inquire as to what makes that age so unique.

151. When do you want to retire? What do you want to do when you retire?

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This is a good question since it gets to the heart of what they actually want to do. That’s not what they’re supposed to be doing. You may learn a lot about a person by finding out what they want to do when they aren’t forced to perform anything specific.

152. What is the most heartwarming thing you’ve ever seen?

Something from reality would be preferable, but if they can’t think of anything, they can turn to movies.

153. What lie do you tell most often?

We all lie to ourselves; the challenge is recognizing the lies and detecting them. Hearing the lies they tell themselves may assist you in confronting the lies you tell yourself.

154. How do you hope you’ll change as a person in the future?

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This question appeals to me since it is a positive approach to discussing flaws. It focuses on improvement rather than just the negative aspects.

155. What could you do with two million dollars to impact the most amount of people?

The emphasis here is not on whether they will be impacted positively or badly, but rather on the sheer number of people. Could you accomplish something that would have an impact on everyone on the planet?

156. Is teaching a skill that can be taught?

Is it true that good teachers are born or that they are made? Is there anything inborn that makes a person more likely to be a good teacher? This is a fantastic starting point for a variety of conversations.

157. What do you think of homeschooling?

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Homeschooling is growing increasingly popular. And, like with anything, there are advantages and disadvantages. Whether you are for or against it, it is an excellent topic for individuals interested in education.

158. Does technology simplify life or make it more complicated?

This one can sometimes lead to an intriguing conversation about technology and modern living, but if the person lands squarely on one side or the other, there isn’t much else to say.

159. What food do you know you shouldn’t eat but can’t stop yourself?

Don’t be concerned; I believe we all do. And it’s likely that the person you’re speaking with has one as well.

160. What’s the best thing to do on a cold winter day?

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Indoors or outdoors? Is it fun or warming? There are numerous approaches you might take with this conversation starter.




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