My Top Books on Love, Sex, and Relationships
These books have changed the way I look at love and relationships
“To love without knowing how to love wounds the person we love.”
― Thich Nhat Hanh
Warning: This is not your average book list.
If you want to skip all the reading (weird, because this is a book list after all), scroll to the bottom to get the entire book list.
For everyone else, read on.
These books have been essential reading on my journey to understanding sexuality, intimacy, love, and relationships. They’ve helped shape me to be the person I am today.
This book list represents books that I routinely reference or read through time and time again. I hope you get as much out of them as I have.
However, you might not connect with some of these books. That’s OK.
You’ll love some and hate others. Take what you want and leave the rest.
Some are old and written when we weren’t aware of privilege, gender norms, and other harmful dynamics.
Nevertheless, these books contain nuggets of wisdom designed to help you connect in meaningful ways with yourself and those around you. Enjoy.
Naomi Wolfe’s Vagina: A New Biography
“Every woman is wired differently. Some women’s nerves branch more in the vagina; other women’s nerves branch more in the clitoris. Some branch a great deal in the perineum, or at the mouth of the cervix. That accounts for some of the differences in female sexual response.”
― Naomi Wolfe
Cara and I were driving to Los Angeles to visit her family when she finally had enough of my shit, pulled over in 100-degree weather, and let me out of the car to cool off.
Hard to do during a heatwave, but I got out.
We’d just fought because I was acting insolent (something my grade-school teachers and my family used to call me growing up and something I was still able to be).
Cara was my girlfriend at the time (and now a dear friend that I speak to every week), and she’s partly responsible for why you’re reading this.
She’s been a huge supporter of The Love Drive from day one and has always wanted me to succeed at supporting humans to be the most loving and connected versions of themselves.
When I told her, warily, that I wanted to be an erotic masseur, she was thrilled and delighted.
Today, however, her patience had run thin with me.
She’d been suggesting that I read her book, or at the very least, listen to a podcast episode she’d recorded.
I wasn’t interested, and it became a point of contention.
Cara couldn’t understand why I didn’t want to take her suggestion, and I couldn’t understand why she insisted I read her book.
We were at a standstill.
I’d never heard of Naomi Wolfe, nor did I think I needed to know more about vaginas. I knew enough to get the job done (God, how cringe-worthy is this sentence?)
Wrong. So so wrong.
When I finally sat down to listen to the episode and subsequently to read her book, it all clicked into place — time to add this one to the book list.
What I thought I knew about female arousal turned out to be just the tip (pun very much intended).
What I learned blew my mind open and has deeply affected the way I relate to women sexually.
Cara: I’m sorry, I fucked up; I should have read this when you first suggested it. I love you.
“It turns out that women are designed to have many different kinds of orgasms;
That women have the potential to have orgasms without any end except physical exhaustion;
That if you understand female sexuality, you pace all the action around her;
That while this is a high bar to set, you still want to set it, because properly treated, some women can ejaculate;
That all women can go into […] an altered state of consciousness; that women’s orgasms last longer than men’s;
That memory plays a role in female arousal in a way that is not the case with male arousal;
And that women’s response to arousal and orgasm is biochemically very different from men’s.
We’re like guys sexually in superficial ways, but in many ways we are, sexually, profoundly not like guys.”
― Naomi Wolfe
Here’s what you’ll learn from this book:
- How the autonomous nervous system is related to arousal.
- How to activate ‘The Goddess Array’ to promote and prolong orgasm state.
- Why women’s arousal networks are more like Sao Paolo Brazil during carnival (unpredictable, complex, and seemingly chaotic) and that men’s are more like Manhattan (there’s uptown, midtown, and downtown, and all men are pretty much the same).
Cara and I got together after we broke up to catch up and walk the dogs (her dog’s name is Pigeon, and mine is Roger).
I thanked her for introducing me to Naomi Wolfe’s work and told her how reading her book has inspired me to start looking into providing erotic massages to women.
Back then, I wanted to help women achieve the kind of pleasure Naomi describes, and I thought that armed with the right knowledge, I might do just that.
I started doing erotic massage because I wanted women to experience the kind of touch Naomi talked about. Then, I found that most of my clients weren’t just looking for joy; they were looking for attention, touch, and love.
Most of my clients were touch-starved. They were either divorced, widowed, in sexless marriages, or celibate for a variety of reasons.
What started as a way to bring pleasure to women’s lives turned into a practice of giving love and attention to women that dearly needed and deserved it.
Here are some questions you might be asking yourself:
- Was this legal?
- Did I sleep with my clients?
- How much did I charge?
- Do I still practice?
- Where can I get a message like this?
And I’d love to tell you everything right now, but I can’t.
However, you can listen to this podcast episode where I spill all the beans about this former life. Enjoy; I know you will.
In the meantime, I went to Esalen, a hippy retreat center on the California coast, for a weekend massage workshop. Then, I invited women that I’d met on OkCupid to receive erotic massages as I honed my technique down and applied what I’d read from various books and manuals.
Oh, which books, you might ask? I took a few pages out of this one.
Dr. Ian Kerner’s She Comes First: The Thinking Mans Guide to Pleasuring a Woman
Dr. Kerner’s book has been instrumental in helping my partners, my friends, and past clients achieve orgasms.
If Vagina gave me high-level insight on women and their arousal systems, She Comes First gave me the tools, techniques, and practices on how to touch women. It’s going on the book list.
Major caveat: orgasm shouldn’t be the goal of sex.
Sex is one way to physically and emotionally connect with your partner, and being goal-oriented about sex takes away the spontaneity and the beauty of the act. That said, orgasms are incredible, beneficial to your health, and if I can help my partner have some, well then, I’ll do what I can.
I often recommend this book to both men and women who want to learn more about the female orgasm and how to achieve it.
Who this book might be for:
- Women who complain that their partner doesn’t last long enough in bed (read this book, then invite them to read the book)
- Men who want to learn about the importance of ‘ladies first’ in the context of sexual experiences.
- Anyone wanting reliable, replicable, guidance on how to perform oral sex on people with pussies.
Storytime: A dear friend of mine (my future best man for whenever and if ever I get married) came to me distraught over the recent ending of his relationship.
For reasons unrelated to his sexual performance, his girlfriend had broken up with him. Since they lived together, he needed a place to crash, and I offered him my spare guest room.
For the next three months we lived together, we spent most nights staying up late talking about everything from house music to snowboarding.
And we talked about women, sex, and God.
I’d discovered She Comes First and was excited about the techniques I’d learned in the book.
I told him about the book, and he read it as late-night reading, not planning to put any of it to use because he was still bereft from his recent rupture.
Fast forward a few months when he and his ex decided to get back together, and after a few weeks of living together again, he approached me to let me know that his girlfriend was pissed.
She wanted to know how many women he’s slept with during their breakup for him to upgrade his skills so drastically.
On the one hand, she loved the increase in orgasms, connection, and intimacy they were sharing. On the other hand, she didn’t believe that he’d learned it all from reading a book.
Here’s what you’ll learn from this book:
- A deeper understanding of the clitoral network (including a detailed description of its 18 structures)
- A deep dive on the different types of orgasms available to pussy owners (hint: they’re all another form of the clitoral orgasm)
- How to notice the various signs and stages of arousal
- Communication tools and language designed to help you connect with your partner in a sexy, loving, and respectful way
Erich Fromm’s The Art of Loving
My first real heartbreak came at the age of 30.
Until then, I hadn’t gotten my heart broken, and I was terrified. I knew it was inevitable. It’s a rite of passage you must experience at least once in life (often more than once).
My high school girlfriend broke up with me when she moved away to college (to then marry the very next man she dated), and I was sad but not heartbroken.
My girlfriend of four years and I split up as I was getting sober. We agreed that we’d grown apart, had irreconcilable differences, and that we’d continue our journeys separately (interestingly, she married shortly after that).
Again, I was sad, but not heartbroken.
My next girlfriend and I (you guessed it, she married shortly after that) broke up on a road trip from Calgary to San Francisco.
It was so painful that she ended up flying back to San Francisco from Boise, Idaho, and when I arrived a week later, all her stuff was gone.
Incredibly sad; still no heartbreak.
That came several years later.
My girlfriend, at the time, was footloose and fancy-free. I craved routine and living a grounded life; she prioritized the moment and followed every whim and fancy.
She’d once canceled a date last minute because she’d run into a trio of banjo players in the park and lost track of time. Another, she showed up two hours late because she’d gotten enthralled in cleaning her baby grand piano.
Looking back, I can see that we weren’t a good fit.
Not because we prioritized differently, but because I was immature.
I didn’t know how to love, and I didn’t have a full life.
Our relationship was the most fulfilling part of my life, and I focused so intently on it that I eventually smothered the flame we had created together.
She needed space, and I needed certainty.
That combo made for an unsustainable relationship (funnily enough, I’m finding myself in a similar scenario these days, but with a plethora of tools at my disposal to help me deal with the uncertainty — thank goodness).
Even though we weren’t a good fit together, being with her was intoxicating.
Maybe it was the push-pull nature of our relationship, or that we had attachment styles that made for an exciting combination, albeit a tumultuous one as well.
Regardless, time with her was electric.
And the sex. Oh my god, the sex.
Thinking of her, being with her, and the idea of her filled my chest with electricity.
I’d felt this feeling before; I’d felt it every single time that “I’d fallen in love,” and it’s presence (or so I thought) meant that I was in love.
I was chasing a feeling.
Her dismissive-avoidant (there, I’ve said it) attachment style made it hard for her to stay open.
My anxious attachment style (at the time, and with her) filled me with anxiety and a need for more demands on her time, more clarity, and more incessant relationship processing. I was desperate to understand where we were, what we were doing, and where we were going.
If you wanted to know how I smothered the flame, now you know.
You can mean well and have great intentions and still act overbearing and insensitive.
And it didn’t help that I was (relatively) young and immature.
I hadn’t learned that love is a choice.
To me, it was a feeling that came from my lover — something bestowed upon me by the grace of God.
How naive and impractical.
The concept that love is a choice and an action came much later.
German social psychologist, psychoanalyst, and philosopher Erich Fromm (March 23, 1900–March 18, 1980) wrote in his book, The Art of Loving.
“Love is a decision, it is a judgment, it is a promise. If love were only a feeling, there would be no basis for the promise to love each other forever. A feeling comes and it may go. How can I judge that it will stay forever, when my act does not involve judgment and decision.”
― Erich Fromm
Erich posits that love, like anything, is a skill to be learned and honed throughout life and that it takes effort and knowledge to perfect.
There’s no course on how to love yet, and often our role models fall short of showing us how to love.
“Love isn’t something natural. Rather it requires discipline, concentration, patience, faith, and the overcoming of narcissism.
It isn’t a feeling; it’s a practice.”
― Eric Fromm
You won’t see this in movies because there’s nothing sexy about discipline, concentration, and patience.
None of this sells movies.
Instead, we’re sold a faulty bill of goods telling us that if we find the right person, it’ll all fall into place.
Bullshit. It doesn’t fall into place.
Love takes work; it’s hard, and it’s not for the faint of heart.
Some people are better suited to be with each other.
We have to do the work required to recognize them as someone to work with when that person presents itself.
It’ll be work.
Could I let go of the idea that love is a feeling, and could I wrap my head around the concept that to love someone is a skill to be perfected through my lifetime?
But I needed help from loved ones, a robust support system consisting of coaches, therapists, psychologists, and books.
Here’s what you’ll learn from this book and why it belongs on the book list:
- An exploration of all kinds of love. Brotherly, self-love, the love of God, erotic love, and the love of parents for their children
- What developing a practice of love looks like
- The disintegration of love in western cultures
While we’re letting go of the idea that love is a feeling and that it’s easy when you meet the right person, let’s let go of the view that “falling in love” is, in of itself, romantic.
“Falling in love” is an evolutionary necessity designed to make us have babies, to propagate the species, and to make sure that we keep populating this earth.
Falling in love helps us bond so that when that honeymoon phase is gone, you stick around and begin the real work of loving someone.
Don’t get me wrong; “falling in love” is incredible, and like Susan Piver says, “a one-way ticket to Planet Awesome.”
But falling in love is not love; it’s lust, a complex cocktail of hormones, and the feeling that we’re no longer alone.
We’re finally saved from our ever-present loneliness — but it’s not love.
I realize where I went wrong with my past relationships.
I stuck around until the honeymoon was over, and when those yummy delicious juicy love feelings were gone, I’d assumed that we’d fallen out of love, and that was that.
I’d decided to leave when the real work began.
I chose excitement instead of work. I didn’t know it at the time because I had other excuses as to why this wasn’t working out.
But deep down, and with lots of hindsight, I was running away from the work of loving someone.
M. Scott Peck’s The Road Less Travelled The New Psychology of Love, Traditional Values, and Spiritual Growth
After reading The Road Less Travelled, I developed a better understanding of the challenges of loving someone.
M. Scott Peck posits that falling in love is closer to something called ‘cathexis,’ the concentration of mental energy on one particular person, idea, or object (often to an unhealthy degree).
When I think back on my formidable relationships, I can say with certainty that in the honeymoon phase, the first 3 to 6 months, I concentrated a lot of mental (and emotional, and physical) energy on one person.
It was delicious but also distracting.
I thought of my love object to an unhealthy degree. And here’s the kicker, I was conflating the honeymoon phase with love.
So when the honeymoon phase ended, as they always do, I thought the love had ended.
And I left.
I should have known better, but I didn’t.
There are many definitions of love, but M. Scott Peck’s is my (current) favorite.
“Love is the will to extend one’s self for the purpose of nurturing one’s own or another’s spiritual growth.”
― M. Scott Peck
I now understand love to be an extension of self, not a feeling.
When the honeymoon phase ended, I didn’t stick around to do the work.
If you stuck around and made your relationship work, bravo, I applaud you for doing the work.
I wish I’d known what I know now.
I’d failed to grow my spiritual life, and I wasn’t willing to extend myself for my partner’s spiritual growth (s). I wasn’t ready to do the work required to love my partner.
Wait, it gets better.
“Genuine love is volitional rather than emotional. The person who truly loves does so because of a decision to love. This person has committed to be loving whether or not the loving feeling is present. …Conversely, it is not only possible but necessary for a loving person to avoid acting on feelings of love.”
― M. Scott Peck
Love is active and requires emotional awareness to have distance and objectivity on our feelings of love.
Here’s another way to look at it:
“Love is the free exercise of choice. Two people love each other only when they are quite capable of living without each other but choose to live with each other.”
― M. Scott Peck
Dr. Alexandra Solomon’s Loving Bravely: 20 Lessons of Self-discovery to Help You Get the Love You Want
I didn’t take Love 101 or Relationships 101 in college, and my folks never talked to me about building lasting relationships.
I learned some of it by watching them, but I didn’t have the language available to understand what was going on.
We don’t have the education required to learn this, so we have to learn it independently.
Speaking of Relationships 101. That class does exist at Northwestern University. It’s called Building loving and lasting relationships: Marriage 101, and Dr. Alexandra Solomon teaches it.
If you listen to the podcast, you’ll know that I’m a huge fan of Alexandra.
Her book, Loving Bravely, is a work of art when it comes to keeping your heart open, even when to do so means risking heartbreak.
That’s what it means to love bravely.
Unfortunately, I haven’t found a way to keep love safe. Living with an open heart is inherently risky.
But it’s a risk worth taking if you look at the upside, and when it comes to love — the upsides are infinite.
There’s a list I found floating around the internet a few years back. It’s called “10 Ways to Keep an Open Heart from Breaking.“
Here are my two favorite bullets from that list.
- Realize that some people aren’t equipped to receive the full force of your love. To send it to them may throw their world into chaos. Love these people gently, with your understanding instead of your passion. And know that there are always people who receive you, in full.
- Accept that sometimes your heart’s just gonna break. It’s OK to let it.
Alexandra wrote the book on how to live with an open heart from a psychologist, university professor, therapist, and wife.
She gives us countless tools to deepen our understanding of ourselves, why we love the way we do, and how we can expand our capacity for love.
Starting with three very different definitions of what a soulmate is, and a mind-blowing explanation of dialectics: a powerful therapeutic approach created by Dr. Marsha Linehan called dialectical behavior therapy (2015).
“Dialectics is a complex concept that has its roots in philosophy and science, and it involves several assumptions about the nature of reality: 1) everything is connected to everything else; 2) change is constant and inevitable, and 3) opposites can be integrated to form a closer approximating to the truth (which is always evolving).”
The last point has particular significance in learning to love bravely, deeply, and intimately.
Let’s look at some examples:
- I feel both excited and afraid.
- This moment is full of both joy and sadness.
- I’m both feminine and athletic.
- I can be both rational and emotional.
- My partner is both whole and a work in progress.
- Both my point of view and my partner’s point of view makes sense.
The idea of dialectics came early in my relationship life.
My girlfriend and I, at the time, sought counseling because we couldn’t figure out how to resolve conflict healthily.
I would raise my voice, and she would shut down — a familiar pattern, but not a useful one.
When I was angry, I couldn’t see why we’d gotten together in the first place. At that moment, I’d lost all ability to feel any love for her. I was angry, and there was nothing I could do to change that.
Slowly, throughout our work together in couples counseling, we worked on expanding my spectrum of emotions. I became more aware of what else was brewing inside of me.
I was able to differentiate between different shades of anger. Then I became more sensitive to other feelings: frustration, anxiety, sadness, irritation, ambivalence, joy, compassion, empathy, and love.
I became confused because I’d be both mad at my partner at times and had compassion for her. I was entering into new territory.
I’ll never forget what my therapist told me that day.
“Having multiple competing emotions at any one time about a person or situation is a sign of emotional maturity.”
― Dr. Jay Talkoff
Oh, thank God.
When you tune into what’s happening and take a breath and a step back, and remember that your partner is not your enemy, you can learn to identify a richness in what you’re feeling.
Sometimes it can be a duality, this and that, but other times it can feel like a whirlpool of emotions.
That’s good. Invite them in, sit with them, and let them move through you.
Remember, having many competing emotions is a sign of emotional maturity.
Susan Piver’s The Four Noble Truths of Love: Buddhist Wisdom for Modern Relationships
“To enter a relationship for the long term is to enter the space of not knowing. While this is so brave and beautiful, exhilarating even, it is not particularly comfortable.”
― Susan Piver
If you listen to the podcast, you know how much I respect and admire Susan. Her work has been instrumental in showing me a new way to love.
Her book is the first written from a Buddhist meditation instructor’s perspective, who is also a wife.
She took the four noble truths of Buddhism and applied them to love and relationships. I can say with certainty that it has transformed the way I understand love and how I relate with my partner.
The idea that all relationships are unstable and that our desire to make them stable is the cause of our relational suffering was a great mind and heart shift for me.
Relationships are hard, and making sense can ease the inner turmoil that we often experience when the going gets tough.
But what about when we can’t figure out what’s going on? How do we stay present for what is, when we’re not sure what’s going on or where we’re headed?
Or what about when we’re head over heels for someone, and we can’t figure out how to make a relationship work? How do we navigate wanting to be with someone when the two pieces don’t fit?
Susan has an answer.
“Just because you love someone doesn’t mean that you’ll love life with them. “
― Susan Piver
Ouch. I learned this lesson the hard way, many times over.
And at the same time, what a freeing thought. Some folks aren’t meant to be in your life full-time, and you aren’t supposed to build a life together.
You can have a love affair with them and part ways when the time is right.
Easier said than done, but it’s valuable to know that we can love people and let them go simultaneously.
Letting go of a relationship that no longer serves you is hard work.
A few weeks ago, someone asked me how to let go and move on from a relationship.
Look at letting go like a meditation practice.
First, you decide to let go of the person and the relationship.
Maybe you’ll feel great about this decision, or perhaps you’ll feel so crummy it hurts, but deep down, you know it’s the right move for you.
There are good chances that you’ll also feel empowered because you’re the one choosing to choose yourself.
And then, all of a sudden, your mind takes that decision back, and you start thinking about “what ifs.”
We got back together?
It was different?
I’ll never find anyone else?
This is as good as it gets?
And then you let it go again.
You keep doing that until, eventually, it gets easier. And it will. I can almost guarantee it.
But, and this is a huge but — it’ll take time, practice, and training.
And it’s fucking hard.
And the contemporary Buddhist teacher Pema Chödrön tells it like this:
“Let the hard things in life break you. Let them affect you. Let them change you. Let the hard moments inform you.
Let this pain be your teacher. The experiences of your life are trying to tell you something about yourself.
Don’t cop out on that. Don’t run away and hide under your covers. Lean into it. What is the lesson in the wind?
What is the storm trying to tell you? What will you learn if you face it with courage, with full honesty and lean into it?”
― Pema Chödrön
A word to the wise:
Most of the wisdom you’ll find in the world is contradictory. The best way to approach all learning is to take it in, sit with it, and integrate that which makes sense to you.
Take what you want and leave the rest.
Some of these nuggets will fit better than others. Some will feel downright awful to you, and that’s OK.
Leave them behind (or recognize them as the next phase of your development.)
You might even experience cognitive dissonance. That’s OK.
Leave it behind.
These books, these nuggets, and these learnings are here to help you make sense of this mystically complicated subject we call love.
Love is intensely personal.
I invite you to create your definition of love.
One that you feel so deeply in your core that nothing can shake it.
Nothing I say, or these other folks can say, can make you doubt what you know to be true.
For the sake of (relative) brevity, I’ve stopped my musings on these books here and included a complete list of books I recommend. Enjoy!
The (in)complete list of books on love and relationships (updated January 2021):
The State of Affairs: Rethinking Infidelity by Esther Perel