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My Favorite Books on Dating & Relationships

Over the years, I've read a lot of dating and relationship books.

In fact, reading dating books was actually something of an embarrassing obsession that chased me through my twenties - from college, through the gap year during which I dated prolifically, through to graduate school (where I was supposed to be reading film criticism), and then on into my first "grown up" job, where I finally got into my first long-term relationship and stopped needing to read them.

Nevertheless, she (I) persisted (reading dating books, for some reason).

It was my disconcerting dating-book habit - which continued even long after I needed such books for actual dating advice - that clued me in to a personal realization that maybe I should do something with all of the information and theories about dating that I had collected over the years.

Where was I going to put my obsession with dating and attraction? At this point, my interest had clearly transcended my own experience of dating to reach an almost academic fervor - a personal study, if you will, of human dating behavior.

A handful of years later, and here I am. Slightly older, marginally wiser, and now a full-time, professional dating coach, writing a blog post on my favorite dating and relationship books.

What follows is a list - in no particular order - of my personal favorite dating and relationship books that have earned - through extensive reading and rereading - their place at the top of my bookshelf (and of my Audible queue).

Attached: The New Science of Adult Attachment and How It Can Help You Find - and Keep - Love (Amir Levine and Rachel Heller)

What it's about:

A research-informed read on attachment theory and its three types - secure, anxious, and avoidant - that can benefit both singles and those in committed partnerships alike.

Why I love it:

It does a good job at explaining a useful theory. While attachment theory tends to be over-cited by coaches and therapists as a cure-all approach to relationship woes, and has consequently gotten something of a bad rap in the personal development space, it's still a valuable framework that can, in fact, explain a lot. I still use attachment theory in-session regularly, and while Levine and Heller didn't invent the theory, their book does a remarkable job of unpacking it.

Who should read it:

  • You, if you feel like you're constantly dating, but are wondering why relationships don't "stick" for you.

  • You, if you seem to end up in a lot of new relationships, but few lasting relationships.

  • You, if you feel like your relationships are always chorus-of-angels-singing amazing or seventh-circle-of-hell terrible (sometimes within the same couple of hours), but never just "good."

  • You, if you tend to experience a lot of anxiety around dating and relationships.

Mating in Captivity: Unlocking Erotic Intelligence (Esther Perel)

What it's about:

Written by renowned couples therapist Esther Perel, this book is a thought-provoking exploration of monogamy and sustaining desire in long-term relationships that challenges how we normally think about both. The book draws on Perel's decades of experience as a multicultural couple's therapist, and combines stories from client data with a deep knowledge of the relevant literature in the field to draw fresh and challenging conclusions about how we think about desire and sustained love.

Why I love it:

Much like its subject, the book itself is defined by paradox: both research-based and gracefully, poetically written, both driven by data and punctuated by stories, simultaneously weaving a coherent theoretical web and leaving space for the ambivalence of love, lust, and desire.

Who can it help?

  • You, if you're in a long-term relationship and looking for ways to "revive the spark."

  • You, if you associate the word "commitment" with the phrase, "no more sex."

  • You, if you've recently come out of a long-term, passionless relationship and you want to conduct a post-mortem.

  • You, if you feel uncomfortable, squeamish, or bored even just thinking about the possibility of a long-term relationship.

The State of Affairs: Rethinking Infidelity (Esther Perel)

What its about:

Another one from Esther Perel, and definitely worth the read. A interrogative look at affairs from the perspective of a couples' therapist. Backed by decades of data from real-life couples in Perel's New York practice, the book explores the titilating subject of affairs, probing for what they may have to tell us about how we participate in modern relationships.

Why I love it:

Like Mating in Captivity, The State of Affairs is both confronting and deeply empathetic, grounded as well as enigmatic. Before reading, I saw affairs as relatively uncomplicated - affairs were cruel, they were easily prevented (just break up?), and they were deeply wounding - even traumatic. This book blew my previous understanding of affairs wide open in its nuanced exploration of long-term relationships, desire, the thrill of transgression, and the excitement of erotic vitality - all of which helped me to better understand the complex history of why affairs, like partnerships themselves, are a long-standing romantic institution.

Who would benefit from this book:

  • You, if you've currently or previously been impacted by an affair.

  • You, if you're looking to better understand the motivation and circumstances surrounding affairs.

  • You, if you're interested in a philosophical and poetic exploration - that is still deeply grounded in experiential data - into what makes sex sexy.

The Seven Principles for Making Marriage Work (John Gottman, Ph.D., and Nan Silver)

What it's about:

A marriage and family therapy staple, this 1999 book was the product of decades of couple's research conducted by Dr. John Gottman and his wife, Dr. Julie Gottman, in their "Love Lab" in Seattle. In the book, Gottman summarizes key findings from his long-term research on couples into seven principles of marriage that each get their own chapter. The book emphasizes partnership, personal responsibility, and a shared vision for the relationship as the basis for successful long-term partnerships.

Why I love it:

Pretty much every couple's therapist has read and will recommend this book. For good reason, it's one of the best-known books in couples therapy - in part because it's so extensively research-based. The Gottman's work on marriage is the majority of the available research on couples and on long-term relationships, and while other research exists, this book summarizes much of what's been done. Moreover, while the book is evidence-based, and contains context on the Gottmans' work in research, the text itself is very accessible and reads as a handbook for couples, making it a great read for you, your mom, your best friend, and your sister-in-law who's relationship is in trouble (but maybe don't get involved in that).

Who would benefit from this book:

  • You, if you're in a long-term relationship (marriage or not).

  • You, if you ever want to be in a long-term relationship and be happy about it.

  • You, if you had a terrible long-term relationship or relationship of any kind that you regret, and you want to conduct a post-mortem.

  • You, if you value research and like science, and want an evidence-based perspective on longevity in relationships.

The Love Gap: A Radical Plan to Win in Life and Love (Jenna Birch)

What it's about:

A dive into modern dating culture from a research-informed, woman-centric perspective. In her book, Birch investigates the question, "Why does the modern, accomplished, 'full-package' woman struggle in dating and relationships?"

Why I love it:

This book is a mix of theory and practical advice for the modern, career-driven woman - smart, independent, and successful - who feels like she should "have it all" but struggles to find love.

Who would benefit from this book:

  • You, if you identify with Birch's target demographic: smart, successful, single "full-package" women who at some point have heard the infuriating words, "You're going to make some guy really happy one day."

  • You, if you're ambitious, career-driven, and goal-oriented, and are confused about why the same principles that work in every other aspect of your life haven't seemed to work in dating.

  • You, if, in a petty moment of brutal honesty, you ever find yourself looking at your less-accomplished female friends (who didn't even really try that hard at dating!) and wondering, "How on earth did THEY end up in great relationships?"

Marry Him: The Case for Settling for Mr. Good Enough (Lori Gottleib)

What it's about:

A book that I avoided for years because of its off-putting title, but is actually a highly insightful reflection on the expectations we bring to modern dating, from journalist and therapist Lori Gottleib.

Why I love it:

I went into this book expecting to hate it, but ended up not wanting to put it down. There are parts at which I found myself wincing in uncomfortable recognition - Gottleib does a excellent job breaking down modern dating expectations and entitlement - we all want "the best" according to an objective standard, but we haven't all put serious thought into exploring if we're also "the best." Gottlieb's book also gives a painfully honest first-person account of the challenges of dating as a woman after 40.

Who would benefit from this book:

  • You, if you're a woman dating in your 40's and beyond, and just want to read something that isn't going to try to convince you that dating isn't terrible.

  • You, if your friends think you're "picky," but you think that you have standards.

  • You, if you tend to take a "list" approach to dating - you have a list of qualities that you want in a future partner, and you tend to date "on type."

  • You, if you have an eagle eye for "red flags" when you're dating, and the idea of dating anyone wearing a polka-dot bow tie in their profile photo makes you squirm.

Models: Attract Women Through Honesty (Mark Manson)

What it's about:

A lesser-known early title by New York Times best-selling author Mark Manson. While the book was written as a kind of response to mainstream men's dating advice, its advice on authenticity and compatibility in dating is universally applicable.

Why I love it:

This is THE book that convinced me to date authentically. It's also the book that convinced me that dating authentically doesn't need to mean not having "game," and that "authenticity" isn't the same thing as you showing up to a date in your stained sweatpants and Crocs, screaming about your ex for an hour and then being confused about why your date wasn't into it. This is also the book that I recommend to many of my male clients as a jumping off point to our work together, and it covers all aspects of the dating process - from beliefs around dating and sex to becoming a universally attractive person to a "how-to" guide to being a good kisser.

Who would benefit from this book:

  • Men who are dating.

  • You, regardless of your gender identity, if you want a well-written and no-BS guide to authenticity, dating, and what makes people attracted to other people.

  • You, if you've read any kind of Red-Pill/Manosphere/PUA content and feel like it's not fully gotten you to where you want to go.

  • You, if you value authenticity, but still want to have "game."

  • You, if you date men and want an "inside look" at men's dating advice.

Beyond the Breakup: Understanding Your Ex-Boyfriend from the Male Perspective (Andrew Aitkin)

What it's about:

A book that helped me through many a breakup of my own back in the day, and that now informs how I work with clients around breakups. This book is something of a one-hit-wonder from a successful blog author, but it's one of the best straight-shooting books on breakups I've read.

The book is an extension of the author's popular "The Rules Revisited" blog, expanded and reworked as a comprehensive primer on understanding, dealing with, and learning from breakups, specifically the variety of breakups initiated by American heterosexual men.

Why I love it/a disclaimer:

Before I can recommend this book in good conscience, it needs to be said that the author's blog follows the brand of advice popularised by The Rules books in the 90's, which contemporarily shows up in the internet's "Manosphere/Red Pill" philosophy. While the author's message, unlike the advice in the "Manosphere," is directed toward and meant for women, be warned that the advice in this book isn't for everyone.

There are a lot (a LOT) of heteronormative, gender-based assumptions in the book that will hands-down not work for couples in relationships with non-traditional gender scripts. While the other books I've recommended more or less reinvent those scripts, this is the book that's going to make evident what those scripts are. So - proceed at your own peril.

That said, this book is hands-down the best advice I've read for women on the unwritten social code underlying traditional, gendered dating scripts. If you're a woman who is dating men, and you're interested in learning the "rules of the game," even if you only want to know them before you break them - this book is for you.

Who would benefit from this book:

  • You, if you're a woman who is dating men, and who wants a relationship with more or less traditional gender roles. Bonus points if you've recently been through a breakup.

  • You, if you're a woman dating men and want to understand, generally, how American heterosexual men see dating and relationships broadly.

  • You, if you're a woman who is dating men, and you're interested in learning the unwritten social code underlying traditional, gendered dating scripts - even if you only want to know it before you ignore it.

And that, folks, is all she wrote. But not all that she read. Now that I've broken the ice on writing book recommendations, I think I'll be writing another of these on my favorite personal development books - and most likely soon. Stay tuned.


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