One Simple Habit To Crush Any Conversation: From CEOs To The Woman In The Bar

Today, we’re going to completely strike from the face of the earth an uncomfortable experience we’ve ALL had….

I’m good in the first few minutes of conversation, but how do I keep a conversation going and keep the other person really interested? How do I stop it from stalling?  How do I deal with silences?

Have you been there?  Me too.  You’re having a conversation with someone and it’s going great.  Maybe it’s the CEO of the company you want a job at.  Maybe it’s the beautiful woman you’re talking to at the bar. Suddenly conversation starts to stall and you’re thinking “what do I say next??”.

Today I’m going to teach you to cut those awkward pauses out at the root.  No longer will you search for interesting things to say every 30 seconds! You’re going to have conversations that flow naturally and easily, regardless of who you’re talking to.

Here’s the deal: conversation doesn’t stall IMMEDIATELY.  It usually lasts a few minutes, you get the basic stuff out, then twiddle your thumbs because neither of you has anything left to say.  Or more accurately, because neither of you engaged the other enough to inspire further conversation. Then the CEO or the woman or whoever it is you’re talking to excuses themselves politely and finds someone else to speak with.

Bummer.  But it didn’t have to end that way.  Because you had a huge opportunity to really grab their attention.  How?  With this question, that comes up in almost every small talk chit chat conversation:

Where are you from?

And I would bet you answered something like this:

“New York.”
“Oklahoma, but I live in Philadelphia.”
“My parents are Korean, but I grew up in Florida.”

And that my friend, is where you shot the conversation in the foot and left it to limp to its ignominious death.

Don’t wanna do that?  Soldier onward.  The answer lies ahead.

Hint hint: You don’t need more questions.

You need to take those questions that are GUARANTEED to be asked in the first 5 minutes (like “Where are you from?”) and answer them in a way that makes the other person want to continue the conversation.

Take the “gimmes” and knock them out of the park

Let’s say you’re like me and your basic answer to, “Where are you from?” is “NYC.”  The only shot someone can respond enthusiastically to “NYC,” is if they lived there, want to, or know someone who does.  Luckily for me, a lot of people fit that criteria.  But if they don’t, there is nothing left to say.  And it only gets worse if you’re from Columbus, Ohio, or some place most people know nothing about.

(Sorry, Columbus – you know it’s true).

So give the person you’re talking with some conversational ammo they can use.


“Well I used to live in NYC, but now I live in Rio.  I loved NYC, but the weather sucks for 8 months out of the year so I can’t do the outdoor stuff I like.  And even more importantly the people in Rio have something that New Yorkers don’t, which is why I moved.”

Now you have interesting conversational threads for this person to pick up on.

How did you pick Brazil?
What kind of outdoor stuff do you like?
What is it about the people from Rio you like?
What is it that New Yorkers lacked?

All these are logical questions that people WILL ask.  You hinted at something fascinating, but didn’t pull back the whole curtain.  Their own psychology will make it near impossible for them not to ask more.  And now they are solving the awkward silence problem for you!

How to REALLY turn “Where are you from?” into a killer conversation

Obvious truth coming: no one really cares where you are from.

It is a conversational crutch. They are being polite or hoping for a commonality. “You’re from Oklahoma!? No way, I grew up there, too.”

Really, the only thing they care about is WHO YOU ARE. Who you are is not where you are from. And believe it or not, it isn’t what you do either.

It is WHY you do the things you do.

So if you’re from NYC, but currently live in Rio (like me), explain WHY you’ve chosen to live there. Take my previous example:

“Well I used to live in NYC, but now I live in Rio. I loved NYC, but the weather sucks for 8 months out of the year so I can’t do the outdoor stuff I like. And even more importantly the people in Rio have something that New Yorkers don’t, which is why I moved.”

90% of the time people will ask…

What do you like about Brazilians?

…and NOW I get to reveal my values. This is where people get drawn into your world.

“New Yorkers are cool, but their priorities center around their career. Last year I got sick of it and visited Brazil. And it was immediately clear how some Brazilians–not all–were just so much more loving and alive. They smiled bigger, touched one another all the time, were incredibly loving and affectionate. I can’t stand people who are guarded. And while not all NYCers are one way and all Brazilians are another, I found more of that loving, friendly nature here so I had to move.”

Look at the values I included:

  • Loving, friendly, open people
  • Adventurous – I left NYC on a whim
  • Freedom – I’ve set up my life so that I have the ability to live anywhere in the world

With those few sentences this person knows more pertinent information about me than they would if I read them my resume line by line.  And chances are, while our biographies may not be similar, we can now connect on our shared values.

A note on oversharing

You’ll notice that in the above example, I don’t immediately overshare.  I give a 2-3 line response to their initial question, and only dive deeper once they ask further questions.  If they don’t ask, I don’t tell.  I’m not trying to force feed them my worldview.

But they do ask 90% of the time, because I leave open loops.  Conversational bait which prompts them to want to know more.  Do the same. Because now…

We’re going to create your new, engaging responses

Yes, that’s right, it’s your turn!  We’re going to retrain your old habits so that when people ask you about yourself, you’re revealing values instead of boring facts.

This is going to help you across the board.  It will help you turn a business meeting into a job offer.  A chance encounter on the subway into a blossoming friendship.  A stalling conversation at a bar into a second date.  Every conversation improves when you reveal your values.

So to start, write out your values. You can use the ones I’ve listed as inspiration, but make sure the ones you write are true for YOU. Here are a few to get you started:

  • Friendly
  • Decent to all people
  • Effusive in their happiness
  • Funny
  • Intelligent
  • Non-judgmental

Write down at least 3.  Seriously, do it.  This is a waste of your time if you leave it as a theoretical exercise.

Take 5 minutes to boost the quality of every interaction you have.

So write at least 3 values you live your life by or want more of in your life.  Got ’em?

Cool.  Now pick your top one. You’ll know it is important because it is the one you most want to find in other people. So if you NEED other people in your life to be adventurous, keep that one up top. Personally, I love people who are open-minded and live in contrarian ways, so I often talk about quitting my job to pursue my dreams.  With women that I might want to date, it is very important to me that they are affectionate, so I lead with that value.

Now, answer the following questions in a way that baits your listener to ask for more information AND reveals your primary value.

  1. They’ll say: “Where are you from?” (convert this to “Why did you wind up where you are today?”)
  2. They’ll say “What do you do?” (convert this to “Why do you spend your time doing what you do?”)

Now, get ‘er done!

Did you write down your answers?

If not, take the time.  It will change the dynamic of every conversation and short circuit the awkward silences.  You’ll wind up with more people that are interested in you because more people will know what you stand for.

Now you just have to work those more honest, revealing answers into conversation.  You’ll have more engaged conversational partners. They’ll know what is important to you. And they’ll likely try to prove they have those traits as well. All from changing how you answer 2 common questions. Pretty neat.


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67 thoughts on “One Simple Habit To Crush Any Conversation: From CEOs To The Woman In The Bar

  1. I do something very similar. Whenever someone asks my age or what I do, I always have the same response. I won’t answer the question directly. I say, ” When we first meet someone we tend to ask a few questions, How old are you? What do you do? Where are you from? We ask because we think that these questions will give us an idea as to who this person is. But we all have preconceived ideas, we have stereotypes that we put on people. I don’t usually fit into the pictures that people have in their heads. I prefer a person to get to know me, my personality and then make their decisions about who I am.” This almost always leads into talking about our values and how we see ourselves and others. Of course I do have ways to answer the questions that tend to come up, ie. job, hobbies, favorite band, song, book, etc. My answers are not the boring answers that most people give. Leil Lowndes has great books on communication if anyone is intersested.

    1. Sounds like you’re dodging the question, like you’re ashamed of how old you are or are unemployed.

      Not everything is for magical value sharing. Sometimes you just gotta get information out.

    2. Hi, D Giovanni. Thank you for that author reference!

      I like your intent with your conversation opener, and may I reveal that if I heard it expressed just like that I would feel put off, because I would feel like I was being corrected. I would read into it, “Oh, so you want to use the typical, simple-minded starter questions, when don’t you know, as I do, that there are more important ways to find out about a person.”

      I wish you many good conversations, however they may unfold.

  2. Nice post Charlie. For a while I was annoyed by the question “Where are you from?” and thought that the solution was to say “I’m from Rhodesia.” or “I’m from Peru.” This either made me feel bad for deceiving people, or it made people not trust me because I lied to them within 15 seconds of knowing them.

    Recently I started saying something like this, “Well I was born in California, but I consider Brazil my home now. Brazil just has something special about it that I haven’t been able to find in any of the other places I’ve lived.”

  3. Uh, this was lifted practically word-for-word from the book “How to Talk to Anyone” by Leil Lowndes, including the example of Columbus, Ohio….you could at least give her credit…

    1. I recently read the book, but honestly wasn’t thinking of it when I wrote this and the advice I give is very different from hers. I’ve been teaching my clients the habit I describe in the post for a long time and have gotten more questions on it in the last few weeks, which is what inspired the post. You’re probably right about the words “Columbus, Ohio” slipping in there subconsciously

      I will say, if I remember it correctly, she recommends remembering a fact about where you’re from. That might extend conversation, but what actually allows you to connect with people is the values part.

      1. You acknowledge this is the comments but you still haven’t cited where you paraphrased and haven’t added a bibliography. Stop being a plagiarizing scumbag and fix it.

        1. Here is a link to the book How to Talk to Anyone by Leil Lowndes.

          I’m not citing it because I didn’t plagiarize it and I didn’t paraphrase it. Go reread the chapter that discusses “where are you from.” I just did. Her advice to improve your answer is “Learn some engaging facts about your hometown that conversational partners can comment on.” She recommends starting at the chamber of commerce and talking about your home city’s history.

          This is fundamentally different advice than talking about your values and answering “why” instead of “where.”

        2. Perhaps you are familiar with Albert Einstein Derp. or maybe not. If so, you may remember the quote “To steal from one is plagiarism. To steal from many is research.” Charlie, you, me and everyone else on the planet who has access to internet or books has been inspired at various points in our lives by the ideas/theories/writing of others, and we often combine them to form our own ideas/theories/writings on the world, based on the lens through which we see it, which is in large part determined by the influences we’ve had along the way. Charlie has read extensively on the topic of self-help and self-improvement, and thus his own ideas are a conglomeration of the best of what he has come across and his own ideas for how people can make themselves better. If you asked me, that wold make him the opposite of a scumbag, or certainly of someone who berates another individual on a public website for an imagined offense without having ever met them. So maybe you should ponder that, “derp.” Or should I say Twerp?

          1. Oh, Corey, what a beautiful answer, all the way up to the last, gratuitous sentence. I was feeling, “Yeah! That’s right.” And then, even as I can appreciate the motivation, “Uh oh. Fuel on the fire.” 🙂

          2. I agree..
            I’m sure if you speak to Tony Robbins..he’s honest about his mentors..
            School teachers taught you mostly things they had learnt.
            Putting people down on any level is probably something you may find is related to personality disorders..or an old blue-print programme you haven’t been aware of..but i will suggest that in order to engage in and hold a would be beneficial to research why you feel the need to belittle people..before worrying about how to hold a conversation.
            There’s more to holding a decent conversation..simply being decent is a really good starting point..and by that i mean..
            If you care about people..then you would care to become a better version of yourself first.
            Accept people for who they are..and if they or their contributions don’t line up with who you are..then move on and seek someone you can relate to..and if that person is a match for you..then stick to they a friend..or whatever to you.
            It’s simple stuff..if you feel uplifted or inspired by a person..then they’re a match..if you feel uneasy or uninspired by the person..then there’s no need to give them a verbal lashing..simply move along until you find your suitable match.

        3. Perhaps you are familiar with Albert Einstein Derp. or maybe not. If so, you may remember the quote “To steal from one is plagiarism. To steal from many is research.” Charlie, you, me and everyone else on the planet who has access to internet or books has been inspired at various points in our lives by the ideas/theories/writing of others, and we often combine them to form our own ideas/theories/writings on the world, based on the lens through which we see it, which is in large part determined by the influences we’ve had along the way. Charlie has read extensively on the topic of self-help and self-improvement, and thus his own ideas are a conglomeration of the best of what he has come across and his own ideas for how people can make themselves better. If you asked me, that would make my friend Charlie the opposite of a scumbag, or certainly of someone who berates another individual on a public website for an imagined offense without having ever met him. So maybe you should ponder that, “derp.” Or should I say Twerp?

      2. Nicely written Charlie. That was masterfully said. Even if it was a bit long winded 🙂 Honestly, I often find it difficult to disagree with someone without upsetting them. Your argument was respectful and considerate yet unbending from your convictions. This is why you still have my attention. You not only teach your theories, you live them.

  4. What if the journey isn’t all that interesting? For example, I left my home state for college. So my ‘why’ is fairly mundane, except for the actual school I chose (but it seems like a bit of a stretch to answer this question with ‘why I chose this school’.

    1. Definitely not a stretch. A stretch is to try and run a conversation off boring facts. So you could say something like, “I’m from X state, but I wanted to come to Y college, because I love the style of life here/the program the offer is what I love doing.”

      It’s totally appropriate to answer why this school (Assuming you do it in 2-3 sentences and don’t ramble). You’re doing the person you’re speaking with a favor. They don’t know what to say, which is why they asked you “Where are you from?” in the first place. You’re helping them move the conversation towards the good stuff.

  5. Charlie, that was an excellent post. It’s so simple… yet so overlooked. I did the 2 exercises and I’m pumped to share my values more explicitly when meeting new people. Cheers!

  6. yeah thanks charlie for all the nice insight, sometimes i think directly telling others about my values are good too as in it gives a clearer information to the others. like example, “i’m adventurous and i like to travel to alot of places” and “i’m usually caring and i usually like to take care of all my friends”

      1. Yes! Great article, Charlie, and nice discussion by all (in the main). Tydus, when Charlie says examples are good, it reminds me of the advice for writers, “Don’t tell; show.” So, for example, a person hearing a claim of certainly values might think, “Oh really? Says you.” Whereas a story that incorporates a value leads one to ask, “Oh, you did/saw/do/find/…? Tell me more!”

  7. Great post. Not only does revealing more about yourself provide the other person a launching pad to ask you questions, but it also shows them that you have interest in learning more about each other. It’s more genuine than a typical, mechanical, 3-word response.

  8. I’m struggling with this exercise because my answers don’t relate to my values. My living in Michigan has nothing to do with my values, it’s only because I was born here.

    1. Great point you raise. The way I see it there are two potential situations you’re in:

      1) You decided to stay. In which case get in touch with the reasons you’ve decided to stay, potentially family, friends, etc
      2) You are just floating through life. You’re not making the most important decisions, but are a passive participant in your life. In this case it is going to be difficult to be charismatic. The recommendation I would give is to actually pick where you live and what you do. You have to live by your values before you can share them.

  9. Great article Charlie! Followed the exercise and look forward to seeing how people respond to my new answers. I’ve always considered those questions a bit of a social experiment and change my answers all the time.

    Your advice to the commenters is excellent as well! Keep up the great work!

  10. Nice post, Charlie. This is real, genuine stuff–learning about yourself, how to articulate your values to others and improving conversational skills all in one exercise. Thanks for this!


  11. This is definitely my favorite post thus far! Not only did it open the door for interesting conversations but it also helped me identify people whom I knew I would and wouldn’t get along with based on how they carried on the conversation. Thanks for the articles and I can’t wait to read more!

  12. Hey Charlie,

    Just saw you over at SJ’s site and came here.

    I like the strategy. Good idea on being short and succinct, and getting them to invest more into the conversation by asking questions. Like you said, I think it’s a good idea to let them ask for more.

    Interesting site you’ve got.

      1. it was nice starter to how to do talks, the values example is something like descent and interesting which may even tempt a person to know about whom they are talking too, thanks Charlie for this feed thought

  13. Dear Charlie,
    I’m so glad I came across you and the work you do! I’m very excited to start incorporating these tools in the future and to see how much they help bring life to conversations. Thank you for the great advice! 🙂

  14. Every time someone writes a blog about something like this, it’s to promote their product. Over the years, I have gotten so used to “I’ll give you that in a second” or “I gotta give some back story” and in the end, the content that was promised by the title ends up becoming promised again in the book/video in promotion.

    Charlie, your posts: from Youtube to your website, are like a breath of fresh air. You’ve got clickbait titles with content to follow up on them and I am grateful for that.


  15. Nice exercise!
    I think what I really got out of this post, is that I can steer any question and any conversation in a direction that becomes interesting by listening to my intuition/emotions, which point me in a direction that I find interesting. So really, any question is just a prompt to listen to my intuition and follow the path of conversation that I find most interesting. So if someone asks “What was the last job you had?” I can explain to them briefly what my position was, but then I’m really free to talk about anything, like how managing the front gate of a festival gave me the opportunity to practice my leadership and inter-personal skills, or how working at the strawberry booth at the farmers market helped me to make decisions faster and with more certainty.

    Good exercise!

  16. Any tips to answer “Where are you from?” when I’m from right next to my college which is in the capital and the college is condsidered the best in my nation, everything to imply about my choices and values are pretty self-explenatory. Only things to say that I can think of are that “I live on ‘xyz island’ just across the bay” or to say something about my international background (biracial, speak 7 languages …).

    1. Masa, I can see your challenge. Congratulations on having found a place and University so suitable and so close by. Could you see something like this as being useful, “When I wanted to pursue my interest [Oh, what is that?] I was happy to know and go to the best university, right in my backyard, because it satisfied the things [Oh, what are those?] that I hold dear.”

  17. im from tunisia 🙂
    this is the exercises reply:

    1. gaming
    2. animes
    3. Music
    1. to have fun
    2. to sucses on my future
    3. to have friends love them and love me too
    1. i was at the coffie place with some friends they i know them verry good
    2. im doing that to have fun and didn’t stay too much on the computer alone playing video games

  18. Awesome post!
    Now all I need is some more opportunities to meet new people and introduce myself!
    I’m still in Middle School, and our school is quite small.

  19. Charlie, I’ve been watching your videos for a while but this lesson was the first one I tried to put in practice:

    (Where are you from?)
    I’m from Bellevue, Washington but when I was a teenager I had this profound feeling of not being understood by people in my town. It seemed that people were used to so much wealth and comfort and weren’t willing to get their hands/hearts/minds dirty with much. So I decided to go far far away – NYC – even though I didn’t know much about it and I didn’t end up staying.

    I’m writing this now from Barcelona…thanks for putting yourself out there and reaching your hand out to pull others up with you!

  20. Now there is a question everybody asks and you have given perfect solutions. I simply don’t care if you have taken it out of some book someone else wrote. Simply love your stuff, mostly your YouTube videos.
    I am a High School student, soon to go to a college and got to say, your video on “How to spot dangerous advice” is the most helpful of all! (Well at least to me hehe)
    You have a loyal subscriber for YouTube and a daily reader for this website in me 😉

    Keep doing what you do, give advice from your experiences and take care of yourself 😉

  21. Where Are You FROM?
    I was born in Aligarh but raised in Noida, so i consider Noida as my home and it holds a very close connection to my heart as it fulfills my career needs as im into music.

  22. Hey Charlie!
    Very helpful post ,I had no idea how to cover gaps in my conversations.I took my time ,wrote down my values.I read those 2-3 times.Reading them itself gave me confidence.And guess what,this changed my entire way of approach towards strangers.

    Thanks for helping us.
    I am eagerly waiting for your other posts and videos.

    By the way I am from vizag, India.

  23. Hi Charlie, am from India! I have been following your channel and just signed up for the emails! They have helped me already! The problem am currently facing is that there is this girl I have a huge crush on and I am just so nervous around her that I can’t even start a conversation with her! We have made eye contact and said hi but I just can’t speak to her! What would you recommend I do!?

  24. Hello Charlie, I am from Gadir-Lunga, very little town in Moldova. I am watching your videos about a month and they are very useful for me. now i read this very interesting post, it is realy helpful, thanks for doing this for us
    : )

  25. Great post!Very useful too! I feel like I have so much to share with people,but sometimes the conversation just rans out.That will sure help me.
    By the way,I’ve been seeing a lot of your videos and your content is fantastic.
    And,I didn’t know you lived here in Brazil,that is so awesome!
    Realmente,o Brasil é um país incrível com uma energia que contagia todos aqueles que visitam. 🙂
    PS: Você é um gato

  26. The question “Where are you from?” is easier than most for me to answer in a charismatic way. Because of my father’s job, we move from place to place almost every two years.
    So, if someone asks me where I’m from, it’s become a default for me to answer it with simething like “I’m actually from (insert hometown) but my dad’s in the army, so I’ve actually lived in a lot of places rather than just one.”
    I realise now what a great conversation starter this is. Thanks for opening my eyes to this, Charlie!

  27. I watched the video on the four emotions, and was wondering how to establish respect if you are the subordinate? Like the student/employee, etc.

  28. Hi Charlie,
    Love your articles.
    What did you do to set up your life so that you have the ability to live anywhere in the world?
    I was born, and still live, in Dallas, Texas.

    1. It’s a very long story, but it all started with reading the Four Hour Work Week – that book gave me the blueprint for making a nomadic lifestyle a reality 🙂

  29. I was born in Cape Town, South Africa. I’ve lived in SA my whole life but I’ve moved around a lot, often a new home every year. I love South Africa because we are so different to other nations.

  30. Hey there!
    I’m from Saudi Arabia, Qatif specifically. A lovely city on the eastern shore. I knew about your channel a while ago but only subscribed yesterday after searching on youtube for something and you popped up to me! I gotta admit i was missing a lot of good videos of yours. Thank you for your hep and advice.

  31. Hey Charlie, i`m from Moers a small town near Duisburg, Germany. And as i`m still a student in his last grade i hadn`t the chance of finding my place in the world yet, but i`m really looking forward to go out and get to know the world. Just to leave behind all these who aren`t open minded or focused only on smartphones.

  32. I appreciate the tips on providing a better response when asked Where Are you from? You provide great examples. In your title”CEOs to the Girl in the Bar” in my opinion tends to be a little sexist. Two things, referring to “the girl” in the bar…. woman, person…and as a woman, it’s not something that would appeal to me. My first reaction was, “really?”. It sounds almost like a path for a “pick up” line which to me is different than talking with a CEO or colleague at work.

  33. I think in order to talk about interesting things, you have to do those things first. For example, you are able to talk about how you quit your job and pursued your dreams so passionately because you’ve actually done this.

  34. Per your request, I am from an island in the Caribbean. Its one you may have heard of called Trinidad. Home of the steel pan and pitch lake. Life isn’t perfect down here but Trinidad for the least part has opportunities that grace me with the chance to start my dream life. Also I have looked over the internet and you reveal a unique way of seeing things that I haven’t seen elsewhere. Keep up the good work and know that it changes lives for the better.

  35. In addition to being asked the before mentioned most common questions (where are you from? / what do you do?), I’m invariably asked, without fail, because I’m 6’7″, “how tall ARE you?,” AND “did/do you play basketball?” (actually, I”m asked that question more than all others). My previous typical responses are “6’7” and “I’m a swimmer.” What would be some better alternatives based on this article? I’m thinking something like a joke about the “weather up here” or hitting my head on ceiling fans (the latter being an all to real occurrence)–lol. Any thoughts would be cool.

    Automotive Sales Consultant
    Columbus Ohio — (lol Charlie)

    1. For Ed.

      “Five foot nineteen.” …. say it with a wink. (only works if they have a brain/ sense of humor. ) “No, I didn’t play basketball, I preferred individual competition and was a competitive swimmer back in high school/ college. What about you?:

  36. Charlie asked the dreaded where are you from question😀 so Charlie will get an anwser; Originally I am from my mothers belly like most people are😛. I carry croatian genes yet I’m raised in Sweden. Haven’t been in Sweden for six years since I studied in medical school in Poland. I liked Poland because of the endless opportunity it offered to celebrate different occasions. Alcohol was cheaper than water. Life was a party, it was rarely quiet if you lived in town. So life in Sweden right now is the opposit, calm and quiet. Forest everywhere. Despite both countries being in Europe, big difference in mentality, if you ask me.

    1. Hi Charlie.

      Great post. Opens the eyes. Changes the game.


      I’m a monk from New York City, now based in India.

      Here are my values:

      1. Humble
      2. Gentle
      3. Learned
      4. God Centered
      5. Friendly
      6. Compassionate
      7. Tolerant
      8. Fearless
      9. Purity
      10. Grateful

      The value that I want to focus on is humility.

      1. I am where I am today, because I had a conversation in Barcelona, Spain twenty eight years ago with an India Swami that changed my life forever. I was offered an opportunity to serve a great mission in India. When I asked him, “When should I travel to India?”, he told me, “Tomorrow”.

      2. I spend my time doing what I do because I appreciate compassion. I find it rewarding to serve as a team member in a mission to try to help people holistically and the whole planet, through spiritual education.

      What do you think of these answers as per the exercise?

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