The Books We Read to Get Us Through Every Stage of a Breakup

My mom (who you may know as interior designer mom) gifted me this book by bestselling author and poet Cleo Wade when I was going through a particularly bad breakup. She truly could not have known how the pages would heal me from the inside. It features life lessons and advice on how to deal with heartbreak, grief, happiness, and all the emotions in between. Years later, I still open it up to read a page or two even when my heart is happy and whole. Once I read, “Hearts break. That’s how the magic gets in,” I knew I’d never be the same.

“One of my best friends was recently lamenting how all the self-help dating books she reads feel aggressive…like what she’s doing is wrong. I suggested that she read bell hooks’ legendary tome. hooks intellectually and philosophically defines love as a concept, what it means to love, what it means to fear it. She takes away all the typical fluff about romantic relationships and keeps it simple. While this description sounds vague and complicated, when broken down in hooks’ terms, the idea of love, loving someone, and loving yourself starts to feel a lot clearer. Pick this up if you’re beginning to self-navigate the world without a partner.” –Margo Ghertner, Skimm Reads editor

Meet Andy Dawson. He’s a 35-year-old failed comedian who’s recently been dumped by his long-term girlfriend and can’t seem to figure out why. As part of his quest, Andy ruminates, parties, and attempts to talk to his male friends — who are either partnered up, have children, or don’t have the chops to talk about their feelings in the context of platonic relationships (or all of the above). Alderton is the master of writing about heartbreak, relationships, and doing things on your own timeline — she writes one of our favorite sentimental reads — and it’s endlessly entertaining to read her writing from the perspective of a man.

This novel’s, well, really good, actually. Appropriately so, since the author is a former “Schitt’s Creek” writer who knows a thing or two about humor, plot, and relatable characters. Her novel, which has major Bridget Jones vibes, follows a 29-year-old stalled PhD student as she re-enters the dating world as a recent divorcée. The lesson here is clear: We’re all messy, heartbroken-at-times humans who are trying to connect with each other and the world. It’s witty and charming and perfect for book club.

Pro tip: Do not read romance novels when you’re fresh out of a relationship. Since I had to stay far away from my usual genre for a while, this was one of the first novels I read after my breakup. If you love Nora Ephron’s romantic comedies like "Sleepless in Seattle" and “When Harry Met Sally,” you need to read her comic novel. It reads like the diary of a cookbook writer, Rachel, who finds out her husband is having an affair — even though she’s seven months pregnant. This book had me sympathizing with the main character (while soaking in the bath and crying, naturally), and giggling at her dry humor. Healing, for sure.

Okay, hear me out. While “Wuthering Heights” might not be the most traditional post-breakup read, sometimes you just want to watch the world burn, and that’s what this is. Reading this classic novel is like watching a car crash and not being able to look away — aka, seeing two people who shouldn’t be together fall in love (in this case Catherine and Heathcliff, don’t @ me). If you’re in the bitter depths of heartbreak, it’s nice to see these lovers struggle and in pain, I’ll say it. You’ll lose yourself in the story and have less time to think about your own ending.

This breakout novel won Andrew Sean Greer the Pulitzer Prize, so it’s worth the read for that alone. But it follows the incredibly lovable character Arthur Less on his worldwide journey to find himself after he loses the love of his life. It’s like “Eat, Pray, Love” from the perspective of a 50-year-old gay man, and his descriptions of life and love will have you tearing up and nodding to yourself at the same time.

“If it’s good enough for Ann Patchett, it’s good enough for me. I discovered this one thanks to the author’s Friday 'New to You' Instagram series. It’s one of those books that I finished, put down, and felt a deep sense of heartbreak and elation all at once. It follows Martha, a 40-year-old content creator and writer, who has recently separated from her husband. Over the course of the book, she moves in with her parents, chooses to be child-free, and grapples with her mental health. Mason tenderly and comedically unpacks all the complicated layers of the choices we make as women when society has conditioned us toward other ‘ideals.’ I will never stop recommending this book.” –Margo Ghertner

“I will read whatever Candice Carty-Williams writes simply because she has a way of writing characters that feel incredibly real. Londoner Queenie Jenkins is a Jamaican-British journalist who’s recently broken up with her long-term boyfriend. The breakup is messy and Queenie does whatever she needs to do (including going on countless dates) to get through. This isn’t your typical journalist breakup rom-com (IYKYK) — it’s far more enriching, thanks to Carty-Williams’ conversations on race in the context of romance and the workplace and straddling two cultures, all while navigating heartbreak and self-love. Read this a thousand times through. It’s just that good.” –Margo Ghertner

We can’t get enough of Cleo Wade. In her latest release, the poet (who’s been deemed the “Millennial Oprah”) discusses how to love yourself in times when you feel lost. The chapters are short, and the balance of prose and poetry feels like heartwarming affirmations. We read this in one sitting, but it’s also perfect for reading slowly — and if you read a chapter or two every morning, it’ll feel like starting your day with a literary hug.

“Bridget Jones’s Diary” meets “Everything I Know About Love” in this bestselling novel that spawned a TV show (“Not Dead Yet,” one of our favorites). When Nell breaks off her engagement and moves home to London to start over, she finds that all of her friends are now married with kids. In quippy, diary-esque entries, she shares her new life (she lands a job writing obituaries and meets a spritely 80-year-old widow, Crickett, who becomes a close confidante), her journey toward self-discovery, and her message that the key to happiness is finding joy in your relationship with yourself. Love.

“Olive has had a tight-knit circle of friends for as long as she can remember, but now most of them are pairing off, getting married, and having kids. Olive is at a crossroads: She’s still figuring out what she wants her life to look like and is navigating the choice of being child-free. I’m a firm believer that Emma Gannon’s only novel has not gotten the love it deserves. Whether you’re going through a breakup, have been single for a bit, or are partnered long-term, this is a must read for everyone, because every kind of choice (separate from marriage and children) should be celebrated.” –Margo Ghertner

“Eve Babitz’s 1979 novel is a modern manifesto for the single It Girl. The twenty-something heroine, Jacaranda, gallivants across Los Angeles and New York City in search of inspiration, a sense of purpose, and — you guessed it — sex. Jacaranda runs with a bohemian, deliciously hedonistic crowd, and her picaresque-style adventures in the bicoastal art scene just might spark in you a similar lust for life.” -Caroline Goldstein, Skimm Reads editor 

Written by a scientist and dating coach who works for the very app you’re about to log back into (spoiler alert: it’s Hinge), this book begs the question: What if you didn’t let your brain get in the way of dating? It offers a step-by-step guide to each decision you need to make in order to find someone, from identifying your personal roadblocks to defining what you’re actually looking for in a partner. This book can only increase your chances of finding the right person.

“I don’t typically read nonfiction, but when Margo told me that the legendary Gottmans have a new book out, I knew I had to pick this up. Using decades’ worth of clinical research, they propose that fighting is integral to maintaining a happy relationship over the long-term — you just need to learn how to fight well. The book taught me so much about my fighting style and my partner’s, and how we can use our arguments as a tool to deepen our connection. Beyond that, as the child of divorced parents, this helped me better understand how my parents’ “conflict culture” has informed my approach to conflict so that I can make healthier decisions in my own relationship. Trust me: You’ll get something out of this (even if you’re not currently partnered).” –Caroline Goldstein

Esther Perel is a world-renowned couples therapist, one of our favorite podcast hosts, and a definitive voice on intimacy. In this book, she examines the nature of desire and what it takes to sustain it in a long-term relationship. Reading this before you enter your next partnership will give you a deeper understanding of why your last one may have ended. It’ll give you a bit of closure while preparing you to open your next chapter.

This is a fun read if you’re new to the dating scene and joining dating apps for the first time, or if you’re rejoining them (we’ve been there). It follows Sasha Goldberg, who works for a matchmaker in New York City while navigating her own breakup with the person she thought was The One. It’s incredibly entertaining, relatable, and reminds us that not all relationships are what they seem.

Picture this: You reconnect with your high school boyfriend in Vegas and wake up — you guessed it — married the next morning. Cruel nightmare or dream come true? This book begs that question as it follows high school sweethearts who find themselves in that situation, with a lot to gain from pretending to be together. It’s the classic contract trope in a romantic comedy we can’t get enough of. Psst…speaking of that trope, "Anyone But You" is now on streaming. You’re welcome.

You can judge this book by its cover. “Beach Read” is, yes, the perfect book to bring to the beach (or the slice of sunlight on your fire escape). It centers on a female romance writer and a male literary novelist who rent neighboring beach houses over the summer. When they’re both stuck with writer’s block, they decide to swap genres and the plot thickens. You’re left wholeheartedly believing in love and happy accidents again.