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

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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

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6 thoughts on “14 Best Books on How to Make Conversation with Anyone (2019 Review)”

  1. Thank you so much for this list, this is probably the most comprehensive list I found. I really appreciate the explanation for each book and why I should or shouldn’t buy it.

  2. Thank you so much for this list, this is probably the most comprehensive list I found. I really appreciate the explanation for each book and why I should or shouldn’t buy it.

  3. Great insights, thanks for this! I’ve read #6 “How to Win Friends and Influence People”, and #10 “How to Talk to Anyone”. I agree, #6 is an excellent foundation! And #10 is a bit of a tips and tricks guide, which can be fun, but like you said, not really a book to read start-to-finish. Cheers!

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