When you are trying to improve your skills and chances with older women it can be a little overwhelming. Every book proclaims itself as the best dating book, blogs can be -hit-or-miss, and the forums often only give general dating advice where it can be difficult to determine if the advice is tested and proven. The last thing you want is to invest a lot of time and energy in the wrong direction.
After extensive reading and testing of our own, as well as spending a lot of time soliciting recommendations from other men who are successful with older women, we have put together a list of the 7 best dating books you will find. These books will make a huge impact on your ability to attract quality older women in your life as well as engage in fulfilling relationships (they certainly did for us).
Before we give you the list we want to emphasize that reading these books is not a substitute for action on your part. You need to take the concepts you learn and commit to applying them to your life. You will have a fantastic blueprint for success that will require less work on your part if you are consistent and smart about your approach.
The Best Dating Books For Single Men
These are the books that have made the largest impact on our success with older women. While this is not a complete list of the great books that are out there we would love to hear any additional suggestions you might have. Please leave a comment below if you think there is a book we should add.
#1 - Models
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Attract Women Through Honesty
By Mark Manson
It isn't a secret that Models has a huge following among men interesting in improving their success with women. If you spend some time talking to a large number of men who have made a conscious effort to improve this area of their lives there is a very good chance that many of them have read this book and almost all will speak highly of it.
Models is a comprehensive guide to attracting women that does a fantastic job of integrating attracting, behavior, and evolutionary psychology into an interesting and easy to read format. Manson is very good at providing a straightforward approach to attraction that is very easy for just about any guy to understand.
Who should read this book (you should)
Honestly, anyone who hasn't read this books needs to. This is the absolute best dating book that you will find and anyone who is searching the internet for dating books (you) is going to come away with a lot of valuable insights. There are few books out there that are nearly universally praised in the way that Models is.
In this book, you will learn both a sustainable way to improve your dating life as well as specific techniques. You can learn the basics--from getting a woman's attention to finally getting the girl you want. Most books on dating and attraction focus on one or the other and no other book really is able to combine them as effectively as Models.
When you read it I suggest you pace yourself a bit. A lot of guys get hooked and devour the entire book in a day. Instead, take your time and think about what you are learning before moving on to the next chapter.
If you are going to read one book on this list this is the one. It has changed the lives of a lot of guys and can do the same for you.
#2 - No More Mr. Nice Guy
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A Proven Plan for Getting What You Want in Love, Sex, and Life
By Robert Glover
Nice guys don't always finish last but they also often don't get what they really want. No More Mr. Nice Guy does not take a stereotypical view of what "nice guy" is. If you struggle at all with personal confidence or your own self-worth this is an absolute must-read book. Most guys don't start out with the level of confidence they deserve when it comes to interacting with women (ourselves included). Instead, there is always substantial or lingering feelings that we are not good enough.
Of all the best dating books out there, No More Mr. Nice Guy does the best job of flipping the concept that you are not good enough on its head. You are not going to find a better book out there for curing "nice guy" syndrome and get you on the right path.
Who should read this book (nice guys)
If you have any feelings of insecurity when it comes to women or shame about who you are, especially when it comes to expressing yourself sexually this book will help you. If you tend to fall back into being a nice guy or best friend with a woman you are interested in instead of acting on your true feelings this book will help you.
One of the biggest problems a lot of guys have is that even if they are spending all their time in great places to meet local cougars they just don't have the right attitude to make the most of it. This book can help.
A warning, this book may be a bit uncomfortable to read at times because it will really open your eyes to your current issues and behavior. Fortunately, you will get clear instruction on how you can address your challenges and actually start working toward getting the girl.
#3 - How to Win Friends & Influence People
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By Dale Carnegie
You might be surprised to see this book so far up on the list but hear us out. It isn't a typical dating or relationship book and isn't the most obvious recommendation for the best dating books to improve your dating life, especially with older women.
However, How to Win Friends & Influence People is absolutely fantastic when it comes to helping you better relate to other people. Put another way, this book can greatly improve your ability to create connections with other people which greatly enable your ability to create attraction with women.
Even though this book has been around for 80 years and sold over 30,000,000 copies the principles have not changed. Millions of people credit this book to greatly improving their professional and personal lives and it will likely have a similar impact on you.
Who should read this book (guys who have trouble relating)
Being able to create connections, relate to women, and carry an interesting conversation are crucial skills that have a huge impact on your success with women. If you are missing any of those three you are really going to struggle in the early stages with most women, especially older women.
How to Win Friends & Influence People does a great job of giving you specific techniques in addition to broader principles. You will be hard-pressed to read this book without a number of highly impactful techniques and mindsets that will make a big difference in your interactions with women.
Give it a read, millions of successful people have to be on to something right?
#4 - The Way of the Superior Man
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A Spiritual Guide to Mastering the Challenges of Women, Work, and Sexual Desire
By David Deida
When it comes to exploring the most vital issues in a man's life, from career to women and intimacy to love The Way of the Superior Man is a foundational book. A personal favorite of ours, this really a practical guidebook for being a man that has a masculine life of freedom, integrity, and success.
If you think the best dating books are about being "alpha" or overly masculine to the point that you become a cartoon character (Johnny Bravo anyone?) you need to reconsider. Nor should you seek to turn into some sensitive snowflake without a spine. The superior man takes the best traits of both in order to live an authentic life that women find incredibly attractive.
This isn't just a "spiritual guide", there are a lot of very practical suggestions that you can begin to implement immediately.
Who should read this book (guys with questions)
A lot of guys get stuck in the trap of thinking that success with women, especially older women, is only one good pickup line away. Unfortunately, that is far from the truth.
If you want to have a great love life, especially in the long term, you need to align your mind, body, and purpose appropriately. You need to be aware of the vibe women are giving off--if they're flirting with you or just being nice. If you don't do that you are destined for failure.
Improving your ability in any area, such as your ability to attract older women, is not an easy task and requires commitment. Just like building a muscular physique requires proper exercise, diet, rest, and discipline so does building a skill set that makes attracting women automatically.
#5 - The Subtle Art of Not Giving a Fuck
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By Mark Manson
This is the second book by Mark Manson on this list and for good reason. When it comes to simply and bluntly laying out the major challenges that men face in dating and in life nobody is really doing it better. This is especially true in The Subtle Art of Not Giving a Fuck.
While Models was a bit more specifically focused on dating and relationships, this book focuses a bit more on creating and living a great life and how that naturally leads to success with women. It's a great book to check out if you want to change your behavior and get women to think about you. A favorite quote from this book:
"And so they settle. They settle and wonder, “What if?” for years and years, until the question morphs from “What if?” into “What else?”
This is a book for guys interested in avoiding that realization 5, 10, or 50 years from now.
Who should read this book (guys who care too much about other peoples opinions)
So much of our success and happiness is derived from our own internal approach to the world and its challenges. We strive so hard for more positive experiences that it creates an overall negative experience for us. Paradoxically, the acceptance of one's negative experience is itself a positive experience! (I didn't write the last two lines, those are in the book).
We all have seen how women often are more attracted to guys who seem to care the least. Sometimes those guys are just assholes but often those guys just don't care about a lot of the irrelevant things that other guys obsess over.
There is a balance to strike between being the selfish asshole who objectifies women and the self-conscious guy who is stuck in his own head. This book will help you get there.
#6 - 
Fundamentals of Female Dynamics
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The Practical Handbook to Attracting Women
By Michael Knight
This is a book that is a bit more technically focused than the others on the list. In fact, Fundamentals of Female Dynamics prides itself on being geared more toward those with technical backgrounds. Men who tend to be more logical in their approach and thinking are really going to love this book.
This book is a very principles-based approach to the problem of attracting women. There isn't going to be a million pick-up lines or tricks that you need to memorize in a particular order to convince a woman to sleep with you. Instead, there are a number of easy to remember principles to guide your thinking and decision making as you interact with women. It's a book full of all the things women wish men knew about them.
Who should read this book (guys who are more technical and/or logical)
The vast majority of the best dating books tend to take a more artisan approach to teaching that a lot of more logical guys have difficulty connecting with. Even though making women want you isn't an exact science by any stretch of the imagination that doesn't mean that it can't be approached in a more logical manner.
If you tend to gravitate to the logical side of the spectrum you are going to be pleasantly surprised with what you find here. This is especially true if you tend to be a more principle or concept based learner. A number of guys that we know who recommended this book are like that and love this book.
#7 - The Art of Seduction
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When it comes to dating books that have stood the test of time few have aged as well as The Art of Seduction. While most of the books on this list measure their lifespans in the single digits (with the obvious exception of How to Win Friends and Influence People) this book has been relevant for nearly two decades.
This is the densest book on our list and expands upon the "twenty-four maneuvers and strategies of the seductive process, the ritual by which a seducer gains mastery over his target". In short, it's all about knowing how to get the girl you want. While we don't necessarily agree with all of Greene's thoughts on the subject he has some phenomenal tactical and strategic advice for guys who are a little further along in their journey.
Who should read this book (guys who are a little more advanced)
Of all the top dating books on our list this is the only one we would really classify as "advanced". Beginners will certainly benefit from reading it but the value really kicks in when you have some experience under your belt.
If you have already read all the other books on this list you are ready for this one.
Psychology Books Guys Should Read
This book came at a handy time. I had to find meaning in my pursuits. I was getting sick of getting grades in school just to be 'useful' to society, as parents, culture and society told me.
The most influential idea I got out of this book is on how negative emotions such as anger, disgust, and jealousy actually have an important place in our lives.
Philosophy books we like
I didn't finish the book, due to its tough prose. It can be quite a depressing read. However, the general ideas in the book left a huge impact on my life and it's a must read.
David Foster Wallace's commencement speech and how to better perceive the daily struggles of life.
