14 Best Books on How to Make Conversation with Anyone (2019 Review)

books making conversation

These are the top books on how to make conversation, ranked and reviewed.

This is my book guide specifically for how to make conversation. Also, see my book guides on social skillssocial anxiety, confidence, self-esteemmaking friends, and body language.

Browse my quick-selection here (Some books are in several categories)

Covering the basics

Also covering general social skills

Advanced conversation skills

Also covers nervosity in conversations

Quick reads

Comprehensive books

Business focused

Honorary mentions


1. A classic covering the basics of small talk.

Conversationally Speaking

Conversationally SpeakingAuthor: Alan Garner

This is one of the cult classics – together with How to Win Friends – and has over 1 million copies sold. It’s about becoming a smooth conversationalist more than anything else: It focuses on small talk with strangers and acquaintances rather than building deeper relationships with close friends.

The language is a bit old (the book was published 1981) but the strategies are great. It isn’t super elaborate on the techniques but is more about giving you a broad understanding. It’s heavily research-based. Sometimes, at the beginning of the chapters, you go “this is way too obvious” but then the author makes a new take on what you thought you know, and that gives you new insights.

Do buy this book if…

  1. You want a conversation classic that’s considered the best in the field
  2. You want to learn the basics
  3. You want something that’s science-based

Do NOT buy this book if…

  1. You are looking for a highly detailed guide. (If so, choose “How to speak – How to listen”)
  2. You are only looking for advice on how to get past small talk to build deeper relationships. (Then I’d also recommend How to Speak – How to Listen)

4.2 stars on Amazon (This is NOT an affiliate link. I recommend this book because I think it’s good).


2. A classic for advanced conversations skills

How to Speak – How to Listen

How to speak - How to listenAuthor: Mortimer J. Adler

Another old-school book, this one from 1983. This is also considered a classic but is more “next-level” than Conversationally Speaking. You could say that this book is about how to take your conversations from “good to great” rather than covering the basics

It sometimes gets a bit long-winded and isn’t as to the point as many other books, but if you have the time, I recommend it.

Do buy this book if…

  1. You already master the basics and want something to take you “from good to great”.
  2. You want a philosophical approach to conversations – a book that looks at the bigger picture and conversations role in the society

Do NOT buy this book if…

  1. You’re short on time and want to cut straight to the techniques. (If so, choose The Fine Art of Small Talk.)
  2. If you want to cover the basics first. (If so, choose Conversationally Speaking. Or, if you want to go even more basic, go for Improve your Social Skills).

4.2 stars on Amazon. (This is NOT an affiliate link. I recommend this book only because I think it’s good).


3. To the point, practical, and with focus on nervosity too

The Fine Art of Small Talk

The fine art of small talkAuthor: Debra Fine

This is a quick read and takes about 3 hours to finish. It’s the perfect conversation book for someone with social anxiety as it covers how to deal with nervosity in conversations.

Be aware that a lot of the examples are in a business setting, even though the techniques can be applied anywhere.

Not all advice is super applicable and it doesn’t go as much in-depth as I think it could.

Some examples in the book are outright tacky, others aren’t super applicable. But on a whole, it’s the best alternative if you want a book that’s fast to read and easy to apply.

Do buy this book if…

  1. You are looking for a quick read.
  2. Talking to people makes you feel nervous.

Do NOT buy this book if…

  1. You are looking for something comprehensive (If so, choose this one)
  2. If you want very applicable advice (If so, I can recommend this free guide)

4.3 stars on Amazon. (This is NOT an affiliate link. I recommend this book only because I think it’s good).


4. The core basics of making conversation

Improve Your Social Skills

How to Improve Your Social SkillsAuthor: Daniel Wendler

This book covers the very basics of social interaction and conversation making. The author has Aspergers which gives this book a different approach to conversations than the other books on this list.

Do buy this book if…

  1. You want to have something that covers the cornerstones of making conversation.
  2. You have Aspergers (Or are on the autism spectrum), or simply want to make sure to build your knowledge from the ground up.

Do NOT buy this book if…

  1. If you are looking for a more advanced take on conversations or have already read up on the basics. (Then, I would recommend The Charisma Myth.)

4.3 stars on Amazon. (This is NOT an affiliate link. I recommend this book only because I think it’s good).


5. Conversation anecdotes in biography-form

How to Talk to Anyone, Anytime, Anywhere: The Secrets of Good Communication

Talk to anyone, anytime, anywhereAuthor: Larry King

This is a book by the 80s-90s talk show host Larry King. He shares what he’s learned after talking to thousands of people on and off camera. Unlike the other books in this list, this one is written biography-form.

In other words, the book is all about anecdotes and not about step-by-step techniques.

Do buy this book if…

  1. You prefer the biography format over the “handbook” format.
  2. You want to learn from someone who’s guaranteed has spent the most of his life talking to people.

Do NOT buy this book if…

  1. You are looking for highly actionable advice on how to make conversation.
  2. You want in-depth advice.
  3. You want a quick read.

4.1 stars on Amazon. (This is NOT an affiliate link. I recommend this book only because I think it’s good).


6. The world’s first self-help book is still a must read

How to Win Friends and Influence People

How to win friends and influence peopleAuthor: Dale Carnegie

This is the first book I read about conversations and social skills back when I was 15. Since then, I’ve revisited it many times, and it’s still a must-read (Even though it was written in 1936!)

Do buy this book if…

  1. You want the best foundations for not only conversations but for social life in general

Do NOT buy this book if…

  1. You want something that focuses only on conversations.
  2. You have social anxiety: The book doesn’t talk about how to deal with anxiety and nervosity in conversations. (I recommend this book for this.)

4.6 stars on Amazon. (This is NOT an affiliate link. I recommend this book only because I think it’s good).


7. Charismatic conversations

The Charisma Myth: How Anyone Can Master the Art and Science of Personal Magnetism

The Charisma MythAuthor: Olivia Fox Cabane

This is a new book compared to a classic like How to Win Friends, but it’s been praised as a 21st-century replacement of that book.

Please note that while there is a chapter specifically on how to talk to people, this book covers much more than making conversation.

Do buy this book if…

  1. You want to be more charismatic in your conversations
  2. If you want a holistic view on social interaction

Do NOT buy this book if…

  1. You want something specifically about making conversations
  2. You want to learn the basics first

4.5 stars on Amazon. (This is NOT an affiliate link. I recommend this book only because I think it’s good).


8. Cult classic on being a better communicator

If I Understood You, Would I Have This Look on My Face? My Adventures in the Art and Science

If I understood you, would I have this look on my face?Author: Alan Alda

This is a classic on being a better communicator (In other words, this is NOT about the basics of conversation, strategies for avoiding awkward silence, and so on)

It DOES cover how to be a better listener, how to avoid misunderstandings, building rapport, and having hard conversations

Do buy this book if…

  1. You want to be better at communicating. If so, this is the gold standard.

Do NOT buy this book if…

  1. You’re looking for the foundations.
  2. You want to be better at small talk and everyday conversation.

4.4 stars on Amazon. (This is NOT an affiliate link. I recommend this book only because I think it’s good).


9. Simple to absorb tidbits about making conversation

How To Start A Conversation And Make Friends

How to start a conversation and make friendsAuthor: Don Gabor

Here’s a basic, easy to apply book for you who want to cut straight to the techniques. Be aware that it seems geared for men who want to talk to women.

It’s written by someone who to me seems to be an extrovert, so the perspective is very different than in, say, Improve your Social Skills.

I think a book by an extrovert can be a valuable perspective if you’re an introvert, but others might feel like it’s a too alien perspective.

Do buy this book if…

  1. You want something simple to read
  2. You want to be better at talking to someone you’re attracted to
  3. You want to learn from an extrovert

Do NOT buy this book if…

  1. You aren’t interested in the “talk to someone you’re attracted to” focus.
  2. You want a more complete book with more in-depth advice
  3. You DON’T want to learn from an extrovert 🙂

3.9 stars on Amazon. (This is NOT an affiliate link. I recommend this book only because I think it’s good).


10. One long list of conversation advice in book form

How to Talk to Anyone: 92 Little Tricks for Big Success in Relationships

How to talk to anyone 92 tricksAuthor: Leil Lowndes

I mention this because it’s a popular book, even though it’s not my personal favorite.

It presents 92 tips for making conversation. This is overwhelming for me who likes to read a book from cover to cover, but I understand that it’s made for skimming and picking the advice you think sounds interesting.

It’s a fast read and quite basic. Most of the advice is business focused.

Do buy this book if…

  1. You like the format of a long list of tips.
  2. You are looking for something business-focused.

Do NOT buy this book if…

  1. You want something in-depth
  2. You are looking for advice on how to make conversation outside of work
  3. You want to learn how to build closer relationships

4.2 stars on Amazon. (This is NOT an affiliate link. I recommend this book only because I think it’s good).


Honorary mentions

11. Conversational Intelligence: How Great Leaders Build Trust and Get Extraordinary Results

A GREAT book, but it’s about how to build trust as a manager or a boss, so it’s outside the scope of this review. Amazon

12. The Conversation Code: How to Upgrade Your Social Skills and Your Life

Extremely detailed, with over 1000 examples of actual conversations, but is uneven in its quality. Amazon

13. Crucial Conversations Tools for Talking When Stakes Are High

Also a great book and a classic, but focused on debates, job interviews, and negotiations. Amazon

14. Emotional Intelligence 2.0

I’ve only read v. 1.0 of this book, which was great. It covers conversations but is more about emotional intelligence in general. If you want to put your conversation skills into context, I recommend investing in this book, too. Amazon

How to make interesting conversation – 17 steps with examples

making conversation interesting

“How can I have more interesting conversations? I get stuck in small talk and bore people and myself”

– Violette S.

I can relate to Violette. After years of studying social skills and reading books on making conversation, here’s what I learned about having interesting conversations.

1. Escape small talk by asking something personal about the topic

We need a few minutes of small talk to warm up. But to not get stuck in small talk, ask something personal related to the topic.

A good rule of thumb is to ask questions that contain the word “you”.

  1. If you have a boring conversation about unemployment rates, you can ask “What would you choose if you decided to completely change job?”
  2. If you talk about how it’s cold outside, you can ask “Where would you rather live if you could stay anywhere in the world?”
  3. If you get stuck talking about economics, ask “What would you do if you had an unlimited amount of money?”

2. Mention topics that interest you and see how they react

If it turns out that you have an interest in common, the conversation gets more interesting for both of you.[1] If they don’t seem interested, you can try with another interest at a later point in your conversation. You might come across mutual interests more often than you think.

They: “How was your weekend?”

You: “Good. I’m taking a weekend course in Japanese which is very engaging” / “I just finished reading a book about the Second World War” / “I started playing the new Mass Effect” / “I went to a seminar about edible plants”

3. Make it your mission to learn 2-3 things about people you meet

It makes the meeting more interesting for both of you if you have a small mission.

It can be to learn what people do, where they are from, and what their future plans are.

Your mission can be to ask people about these things when it feels natural. You get a reason to talk to them and you might find common interests.

4. Share something slightly personal about yourself in between your questions

It’s not true that people ONLY want to talk about themselves. They also want to know who they are talking to. If they don’t, they might even feel interrogated and get uncomfortable.

When we share slightly personal things with each other, we bond faster. [2]

You: How long did you live in Denver?

They: 4 years.

You, sharing something slightly personal: Cool, I have relatives in Bouder so I have many nice childhood memories from Colorado. What was it like for you do live in Denver?

5. Force your attention back to the conversation whenever you get stuck in thoughts

A conversation gets more interesting the more focused you are on it. Bring the focus back to the conversation when you notice that you get self-conscious.

If someone says “I went to Paris last week.”, some start thinking: “Will they look down on me for not having been in Europe? What should I counter with? Is my posture weird?”

If you force your attention back to the conversation, it’s easier to be curious.[3]

Your thoughts when you focus on the conversation: “Paris, I wonder what that’s like? How long did it take to go to Europe? What did they do there? How come they went?”

You: “That sounds exciting! What was it like?”

6. Refer back to something more interesting you talked about before when a topic dies out

Conversations don’t need to be linear.  It’s completely natural to go back to an older topic if the current one feels done and there’s a bit of silence.

They: “So, that’s why I prefer oranges over apples.” 

You: “Oh, I see…”

They: “Yeah…”

Crickets

You: By the way, you mentioned that you were going to a psychology seminar last week, how was it?

7. Ask “What do you like the most about X?” to lead the conversation into passions

Passions are often more interesting to talk about than facts about school or work. If it turns out that you have similar passions, those are great to delve into and form a friendship around.

If someone says that they’re a teacher, you can ask “What do you like the most about being a teacher?”

If they don’t like their job, you can ask “What do you like doing the most when you don’t work?”.

8. Ask open-ended questions

Open-ended questions are the ones you can’t respond to with a simple yes or no.

Closed-ended: Was the vacation good?

Open-ended: What did you do on your vacation?

If you often receive short yes or no answers to your questions, try asking open-ended ones instead.

9. Ask about their dreams

Learning about each other’s dreams makes the conversation more interesting, and you might find dreams you have in common.

You can ask younger people what they want to work with and their life goals. You can ask older people about their plans for the coming years.

They: “I study biology”

You: “Cool, what would be your dream job in biology?”

They: “I’ve been working in real estate the last 40 years”

You: “Wow. Do you ever think you’re going to retire or what’s your dream of doing the coming years?”

10. Ask questions containing “what, why, when, how”

Those questions help move the conversation from small talk to more interesting topics. They often inspire more in-depth answers.[4]

They: I’m from Connecticut

What: What’s it like to live there? What do you like the most about it? What was it like to move?

Why: How come you moved? 

When: Are there times you miss home? When did you move? Do you think you’ll move back?

How: How come you moved?

11. Ask about their personal opinion

It’s fun and engaging to get asked one’s opinion. The conversation that follows is usually more interesting than talking about facts.

I need to buy a new phone. Do you have a favorite?

I’m thinking of moving in with two friends. Do you have experience of co-living?

I look forward to my vacation. What’s your favorite way to wind down?

12. Show that you are interested to come off as more interesting

Use active listening to signal that you are interested in what they have to say. When you show that you are interested, conversations tend to become more in-depth and interesting.

  1. Keep eye contact whenever they talk
  2. Direct your body, feet, and head in their general direction
  3. Avoid looking around the room
  4. Humm when appropriate to show that you’ve heard them
  5. Summarize what they said. They: I didn’t know if physics was right for me so that’s why I started painting instead. You: Painting was more you. They: Yes, exactly!

13. Talk about FORD-topics: Family, Occupation, Recreation, Dreams

When a conversation gets boring, remember the FORD-topics and see if you can ask a related question to any of them.

They: Work is so stressing now because we are undermanned.

You: That sucks. Do you have any vacation plans you dream about?

14. Keep good eye contact to show that you are present

It can be hard to keep eye contact, especially if we feel uncomfortable. But lack of eye contact can make people think that we aren’t interesting, and they don’t dare to open up.

  1. Try to see the color of their iris and, if you’re close, the texture of the iris.
  2. Look in between their eyes or at their eye-brows if direct eye contact feels too intense. They won’t notice the difference.
  3. Make it a habit to keep eye contact whenever someone’s talking.

When people aren’t talking – like when they are having a few seconds break to formulate their thoughts, it can be a good idea to look away so they don’t feel pressured.

15. Figure out mutual interests

Let’s say that you meet this person and she tells you that she works in a bookstore. Just by using that tiny piece of information, what are some assumptions we can make about her interests?

Interesting conversation with emmaI’d say…

  • Culturally interested
  • Prefers indie to mainstream music
  • Likes to read
  • Prefers to shop vintage
  • Vegetarian
  • Prefers going by bike over driving
  • Environmentally conscious
  • Lives in an apartment in a city, maybe with friends

These assumptions might be dead wrong, but that’s OK because we can put them to the test.

I don’t know that much about books, at least when it comes to non-fiction. But I do enjoy talking about environmental issues, and I hypothesize that she might too. So I ask something to move the conversation in that direction:

“What’s your view on e-readers? I guess they have a lesser environmental impact than books, even though I prefer the feeling of a real book”.

Maybe she says “Yeah I don’t like e-readers either but it’s sad that you need to cut down trees to make books” (Or whatever).

Judging by her answer, I will know if she seems to be concerned about environmental impact, and we can now segway into talking about that.

Or, if she seems indifferent, I try another topic.

(For example, talking about if she bikes to work and what bike she could recommend. I’m looking at bikes right now so that’s something I would be interested in talking about.)

Here’s another person you can try with:

Interesting conversation with jessicaYou meet this woman and she tells you that she works as a manager at a capital management firm. What assumptions can we make about her?

Obviously, these assumptions will be very different from the girl above.

I’d say…

  • Interested in career
  • Reads management literature
  • Lives in a house, maybe with her a family
  • Health-conscious
  • Drives to work
  • Has an investment portfolio so is concerned about the market

Here’s another one:

Interesting conversation with TylerThis guy tells you that he works in IT security. What would you say about him?

I’d say…

  • Computer savvy
  • Interested in technology
  • Interested in, well, IT security
  • Plays video games
  • Interested in movies like Star Wars or other sci-fi or fantasy

As you notice, our brain is really good at coming up with assumptions about people.

Sometimes, that’s a bad thing, like when we’re being prejudiced.

But here, we’re using this extraordinary ability to connect faster and make interesting conversation.

What is interesting to us that we also might have in common with them?

It doesn’t have to be the passions of our lives. Just something that you enjoy talking about is enough for an interesting conversation.

Making any conversation interesting, in summary:

  1. Ask yourself what the other person might be interested in
  2. Mutual interests – What might we have in common?
  3. Testing our assumptions – I move the conversation in that direction to see their reaction.
  4. Judging their reaction – If they are indifferent, I try their reaction to some other subject – If they respond positively, we can delve into that topic.

It’s when we find mutual interests that the magic happens.

16. Tell stories in a way that’s interesting

We, humans, love stories. Scientists believe that we are hardwired to like them: In experiments, they discovered that our eyes dilate as soon as someone starts telling a story.[5]

By simply saying “So, a few years ago I was on my way to…” or “Have I told you about that time I…?”, something powerful happens in people’s brains.

You can use storytelling to connect with people and be seen as more outgoing. People who are good at telling stories are often admired by others. Other studies show that stories also will make people feel closer to you by being able to relate to you.

And as time passes, you will have more and more stories in stock.

Recipe of how to successfully tell a good story

  1. It needs to relate to the situation. Memorize your good stories to over time build up a stock. Stories are timeless, a good story can and should be told several times as long as there’s a new audience.
  2. Talking about how good you put people off. Therefore, avoid stories where you come off as being the hero. Instead, stories that show vulnerability prove to work better.
  3. Put people into a relevant context. Explain the setting so that everyone gets the story. More about this in the example below.
  4. Talk about things that others can relate to. Adjust your stories after the audience.
  5. Every story needs to end with a punch. It can be a small punch, but it has to be something. We’ll look at this at the example below as well.

It’s important to realize that people with a lot of stories don’t necessarily live more interesting lives, they just present their lives in an interesting way.

I have a friend who’s an awesome storyteller. When he starts telling a story, people give him their full attention.

Here’s a story that he told me recently:

So a few days ago I’m waking up to an important day with exams and meetings. I’m waking up stressed because the alarm clock had apparently already gone off.

I feel totally exhausted and prepare myself for the day, taking a shower and getting shaved. However, my tiredness just won’t let go and I’m actually throwing up a little on my way out from the bathroom.

I become afraid of what’s happening but I’m preparing breakfast and I’m getting dressed. I’m staring at the porridge but can’t eat and want to throw up again.

I’m taking my phone up to cancel my meetings and realize that it’s 1:30 AM.

This wasn’t meant to be the story of the year – it’s just a great example of a nice story to pull of in a suitable situation.

What I like about this story, in particular, is that it’s not an exceptional event; you’ve probably been through several similar things in your life. However, this guy succeeds in turning it into an interesting story.

Also, notice how you probably felt motivated to read that story more than anything else you’ve read in the guide so far – that’s how hardwired we are to like stories.

Pay attention to the following:

  • He doesn’t try to look like a hero. Instead, it tells the story of a struggle.
  • It ends with a punch. The punch is often the difference between awkward silence and laughter.
  • Notice the pattern. Relatable -> Context ->  Struggle -> Punch

Whenever he’s telling these stories, he gets everyone’s full attention. Through these stories, he makes people feel good and makes them want to be around him. Storytelling is why people see him as an outgoing person.

Click here to read more about how to tell a good story.

17. Learn a path from small talk to interesting conversation

When I start talking to someone, I obviously first present myself:

– Hi, I’m David. How are you doing?

Starting off from the first line, I’m keeping the conversation simple. The simpler you keep the initial conversation, the better it will flow, because it decreases the risk of pauses and awkward silence.

A common mistake people do is trying to come up with something clever to say already in the initial conversation. However, an interesting conversation is not created through smart comments; it’s created by talking about something you both enjoy discussing. And that is what these questions are designed to create. Let’s continue!

– How do you know people here?

This question can be used in most situations where you meet strangers. Let them explain how they know people and ask follow-up questions relevant to what they’re saying.

This question is designed to help gradually transition into a more personal conversation, as it obviously would feel weird to start talking about personal stuff the first thing you do.

In between these questions, share a little bit about yourself once in a while. 

– Where are you from?

This is a good question because it’s easy for the other person to answer and talk about. It’s useful even if the person is from the same town – you can talk about where in town and what it’s like living there. Perhaps you have something in common that you can both relate to about the area.

– Do you work/study?

I ask about either work or studies depending on how old the person is.

Some say that you shouldn’t talk about work with people you just met. And I agree that it’s boring to get stuck in job talk. But knowing what someone is studying or working with is important for getting to know him or her, and it’s often easy for them to expand on.

If they are unemployed, just ask what they would like to work with or study. When you’re done talking about work, it’s time for the next question:

– Is it busy or will there be time for vacation/holiday?

When you’ve arrived at this question, you’re past the hard part. No matter what they reply, you can now ask my favorite question of all categories:

-Do you have any plans for your vacation/holiday?

Now you’re tapping into what they like to do the most. They think about positive things and it’s interesting for them to talk about. Even better, here’s where you might find mutual interests or similar places you’ve been to. Even if they don’t have any plans, it’s natural to talk about how they spend their free time. It’s often possible to find similar interests here.

Click here to read 301 small talk questions to ask friends.

References

  1. Swarat, S. (2008). What Makes a Topic Interesting? A Conceptual and Methodological Exploration of the Underlying Dimensions of Topic Interest. Retrieved from http://ejse.southwestern.edu/article/view/7773
  2. Aron, A., Melinat, E., Aron, E. N., Vallone, R. D., & Bator, R. J. (1997). The experimental generation of interpersonal closeness: A procedure and some preliminary findings. Personality and Social Psychology Bulletin, 23(4), 363-377. https://doi.org/10.1177/0146167297234003
  3. Glanzer, M. (1958). Curiosity, exploratory drive, and stimulus satiation. Psychological Bulletin, 55(5), 302-315. http://dx.doi.org/10.1037/h0044731
  4. Asking and Answering the 5 W’s and H Questions. Retrieved Aug 14, 2019. https://k12.thoughtfullearning.com/minilesson/asking-and-answering-5-ws-and-h-questions
  5. Olivia Kang, Thalia Wheatley. Pupil dilation patterns spontaneously synchronize across individuals during shared attention.. Journal of Experimental Psychology: General, 2017; 146 (4): 569 https://doi.org/10.1037/xge0000271