The 3 Best Dating Books for Men in Their 20s and 30s

I started to succeed with women pretty much from the moment I admitted that I had no idea what I was doing.

As in most areas of our lives, it matters whom we choose to emulate, and from where we choose — consciously or not — to get our information; and my lack of results with women was proof to everyone except me that the information I was getting was dead wrong.

Now, I wasn’t completely hopeless — I was confident and kind, and definitely not ugly (no one should call themselves good-looking); I opened doors for women and asked them questions about their lives (that I actually cared about the answers to); I even went out of my way to make women feel comfortable around me and to show them a good time.

But I wasn’t getting the results in my dating life that I truly wanted, and after reading these 3 books, I was able more clearly to see why.

For example, it used to be a complete mystery to me why, when I told a woman I just met that I drove an expensive sports car (which was true), the lights of attraction would instantly shut down, and her eyes would, in some cases, literally glaze over.

I mean, have you ever seen someone’s eyes glaze over? I had never seen that before. But it was happening every time I opened my big fat stupid mouth. It was actually quite something, now that I look back on it.

Anyway, now that I’m on the other side of complete cluelessness, I can confidently recommend these 3 books to anyone who recognizes themselves in any of the embarrassments above.

Even if you don’t struggle as spectacularly as I used to, you’re bound to come across a multitude of useful and fascinating insights in the pages of these great books.

So let’s see what all these beautiful women haven’t been telling us but wish we knew…

What Women Want, by Tucker Max and Geoffrey Miller

It’s a shame that I read this book so late, because it’s the best dating book I’ve ever read, hands down. Seriously, I took 8 pages of notes, and even though by then I was quite proficient at getting women to become attracted to me, I learned some critical lessons from these pages.

Tucker Max is one of the co-authors, which is shocking because you would think from reading his earlier books that you should absolutely not take any lessons from him, dating or otherwise, he comes across here as insightful and wise, not to mention hilarious. Most of the jokes in the book you can tell came from him.

The book takes an evolutionary psychological perspective, which is Geoffrey Miller’s academic specialty, and together they show that women evolved to prefer certain types of men, with certain skills and traits, and to the extent that men develop these skills and traits, they can become better with women.

Of course there’s a genetic component, and they don’t deny that tall, athletic dudes are going to do way better at bars than shy, generous, kind, introverted men. If the latter describes you more accurately, then bars are most likely the wrong “mating market” for you.

Read the book to learn more about they mean. Honestly, I can’t recommend this book highly enough.

From My Notes on the Book:

“We cannot emphasize this enough: Mating success requires cross-sex insight. You need to understand how women evaluate your qualities and how they perceive the status, danger, opportunities, and threats you could present. The better you learn to see these things from women’s point of view, the less unattractive you will be to them and the less confused, resentful, and frustrated you will be by how they respond to you.”

“Effectiveness is sexually attractive to most women most of the time, but ineffectiveness is sexually disgusting to ALL women ALL of the time. No woman in any culture is erotically attracted to ineffectiveness, whether it’s powerlessness or joblessness or sexual impotence or getting flustered by crises or failing to protect a baby. Thus, apart from cultivating signs of effectiveness, it can be even more important to stop showing signs of ineffectiveness.”

“If you make yourself into an attractive potential boyfriend, then your sexual options become unlimited.”

From Amazon: What Women Want

Models, by Mark Manson

Here’s a subtitle for you: Attract Women Through Honesty! Hey, how about we try that?

I credit this book for turning on its head my entire approach to women and dating. Not that I was being dishonest before, but simply that I wasn’t making it a focal point of my interactions.

Actually, I wasn’t really making anything a focal point of my interactions. I was pretty much just trying to figure out whether she liked me or not. My entire dating life changed when I shifted from wondering whether she liked me, to whether I in fact liked her.

Another major key to this book (and to dating in general) is reducing neediness. Neediness is probably the most repulsive trait you could ever project, and if even I notice it oozing off of tons of other guys at clubs, you know that women are noticing — and getting turned off by — these things too.

From My Notes on the Book:

“The percentage of women who are Receptive to you will increase proportionally to the quality of your lifestyle, your social status, and your looks. The percentage of women that you’re able to move from Neutral to Receptive will be proportional to how good your “game” is, or how well you’re able to communicate and express yourself with women. And your ability to sort through each type of women and meet as many as possible will be determined by how fearless and bold you are when it comes to meeting women.”

“Learning techniques without doing genuine, identity-level work in order to permanently decrease your neediness will only be a band-aid solution.”

“Instead of wondering what to say in order to make her like you, sit silently and wonder what she’ll say next in order to make you like her.”

From Amazon: Models

The Truth, by Neil Strauss

If you’ve read The Game and learned how to “pick up girls,” then read The Truth when you’re ready to grow up.

I have nothing against The Game, by the way. I read it, enjoyed it, took notes, and I’d recommend it to others. To be completely transparent, my dating and mating choices right now tend to short- and mid-term, rather than the long-term commitment that Strauss is testing and exploring in The Truth.

But this book is a painfully honest questioning of the prevalent relationship ideology of “you should go out and find one person to spend the rest of your life with, or else you’re wasting your time.”

This ideology is espoused everywhere, it seems — but it may not be right for you, depending on where you are in your life, what you’re able to contribute in a relationship, and frankly, what you even want out of life.

One of the profound lessons that you can learn from this book, however, is that strong relationships are less about finding the right person, but rather about becoming the right person.

From My Notes on the Book:

“A lack of commitment, too much commitment, a poorly chosen commitment, and misunderstandings about commitment have led to murders, suicides, wars, and a whole lot of grief. They have also led to this book, which is an attempt to figure out where so many people go wrong, again and again, when it comes to relationships and marriage — and if there’s a better way to live, love, and make love. This, however, is not a journey that was undertaken for journalistic purposes. It is a painfully honest account of a life crisis that was forced on me as a consequence of my own behavior. Like most personal journeys, it starts in a place of darkness, confusion, and foolishness. As such, it requires sharing a lot of things I’m not proud of — and a few things I feel like I should regret a whole lot more than I actually do. Because, unfortunately, I am not the hero in this tale. I am the villain.”

“Since adolescence, we’ve been trained as men — by our friends, by our culture, by our biology — to desire women. It seems unreasonable to expect us to just shut it off forever once we get married. Legs are long, breasts are soft, and forever is a long time.”

“The success of a relationship should be measured by its depth, not its length.”

From Amazon: The Truth

The above are three of the best dating books I’ve ever come across, but no doubt there are a multitude of other spectacular ones.

In addition, different authors will always speak more directly to some readers than to others, based on the varying personalities, temperaments, and life experiences we each bring to our reading. Obviously, these three books appeal mostly to men seeking women, but love comes in many forms, and none of those forms are wrong.

I don’t think that you can go far wrong with any of these books though, and there are certainly epiphanies waiting for you in each of them.

Whichever books you read though, whomever you’re attracted to, and whatever your dating goals and priorities, an earnest, conscientious effort to becoming the highest-value, most empathetic, upright and resilient man you can become will serve you well with women everywhere.

I wish you more than luck.

All the best,

Matt Karamazov

Get my Top 20 Unconventional Reading Strategies, which I used personally to read 179 books last year. Download for free here.