Book Recs to My Past Self Regarding The Awful Guys I Dated in My 20s

I’m going to be completely honest here- I was a bit of a disaster for most of my twenties. I drank too much, struggled with anxiety, and was seemingly incapable of making decisions in my own best interest. This was especially true concerning my taste in men. In hindsight, I think I subconsciously expected the “right” relationship to solve the myriad problems I wasn’t ready/willing to tackle on my own. I impulsively started relationships, bulldozing red flags and clinging to romance well past its natural end point. After all, according to my dysfunctional rationale, who cares if you can’t figure out what to do with your life if you’re in love? The quick emotional high of infatuation was a temporary, addictive distraction from the looming chore of “figuring my shit out”.

But eventually, I had to admit that it wasn’t working. I quit drinking. For a while, I quit dating. I went back to school and got a job that was both emotionally and professionally fulfilling. Unsurprisingly, it was only after I started taking care of myself that I met a charming fellow history nerd who shares my love of Jeopardy! and Jon Krakauer.

When I look back at those years, I feel empathy for that floundering, insecure version of myself. I want to hug her and say, “You’re okay! Stop dating guys who make you feel bad! Stop dating -AT ALL- until you take care of yourself!”

If I could travel back in time, these are the books I would recommend to my past self. It’s a grab bag of novels, memoirs, and psychology. Some would help me feel less alone, others would make me laugh, and many would give me the courage to move forward.

I’d like to think there’s an alternate reality somewhere in which Past Me gets an anonymous package with a note in my own handwriting that reads: Here. Read these. It’ll help. 

Book Recommendations to My Past Self Re: Guys I Dated in My 20s 

The College Boyfriend

Americanah by Chimanda Ngozi Adichie

What It’s About:

As teenagers, Ifemelu and Obinze fall in love. Because of Nigeria’s military dictatorship, many people are leaving the country. Ifemelu moves to the United States to study. Obinze initially plans to join her, but his plans are thwarted when he’s denied entry. Instead, he moves to England without legal status. Years later, they reconnect in Nigeria and face tough decisions.

Why Past Me Should Read It:

This story offers one of  the more realistic portrayals of young love that I have read. At the same time, Ifemelu’s relationship with Obinze doesn’t define her. While their love is genuine, Ifemelu moves to the U.S., becomes a successful writer, dates other men, and is a happy and whole person on her own.

To All the Boys I’ve Loved Before by Jenny Han

What It’s About:

Laura Jean hasn’t told any of her crushes that she has feelings for them. Instead, she writes letters to them and hides them in a box under her bed. One day, Laura Jean finds out the letters have been mailed, causing each of the boys to confront her about her feelings.

Why Past Me Should Read It:

When my college boyfriend and I broke up, I took it pretty hard. Like, falling asleep to the dvd commentary of Love Actually every night for months hard.  The letters that Laura Jean writes are less confessional and more like goodbye letters that give her closure when she moves on from her crush. When the guys receive the letters, she has some explaining to do. It’s the kind of light, sweet “what if” book that can be comforting after the First Big Breakup.

Modern Romance by Aziz Ansari

What It’s About:

The amazing, hilarious Aziz Ansari teams up with NYU sociologist Eric Klinenberg and designs a research project that focuses on how people find love in the digital age. They conduct hundreds of interviews and focus groups around the world. The results are as insightful and relatable as they are funny.

Why Past Me Should Read It:

At one point in this book, Aziz describes the ideal initial flirty text exchange. His example was remarkably similar to the actual first texts between my husband and me four years before this book came out. I could have saved myself so much time and effort if this book had been around when I was twenty-two. Plus, it explains things that didn’t exist when I was in college, like smart phones, emojis, and Tinder. Just think of the possibilities…

 

The Cad

The Paperbag Princess by Robert Munsch

What It’s About:

Princess Elizabeth has an ideal life. She lives in a castle and is engaged to the lustrously-coiffed Prince Ronald. That is, until a dragon comes, burns down her castle, kidnaps Prince Ronald, and leaves Elizabeth with nothing to wear but a paper bag. Through a series of clever maneuvers, she defeats the dragon and saves Prince Ronald. Instead of the romantic reunion Elizabeth anticipates, Prince Ronald exclaims that Princess Elizabeth is wearing a paper bag and should come back when she’s dressed like a real princess. Elizabeth basically tells Ronald to bugger off and lives happily  ever after on her own.

Why Past Me Should Read It:

Honestly, this book could fit equally well in any of these categories. Princess Elizabeth is fierce and independent. Prince Ronald is a total dud. Elizabeth’s confident self-sufficiency is an especially resonate message if you’re recovering from a relationship with someone who refused to acknowledge your true value.

Bridget Jones’s Diary by Helen Fielding

What It’s About:

“I will not fall for any of the following: alcoholics, workaholics, commitment phobics, people with girlfriends or wives, misogynists, megalomaniacs, chauvinists, emotional fuckwits or freeloaders, perverts.”

Bridget Jones is a single thirty-something who hilariously chronicles her romantic adventures, professional mishaps, and attempts to cultivate inner poise.

Why Past Me Should Read It:

Daniel Cleaver, Bridget’s colleague and sometimes romantic interest, is the ultimate charming scoundrel. The cad I dated had a similar ability to make me feel singularly captivating while texting other girls on the sly. Bridget Jones’s Diary reminds me that the early spark from a charismatic admirer might be short-lived, but that’s okay. I will find someone trustworthy and reliable, even if it doesn’t feel like it at the moment.

The Mothers by Brit Bennett

What It’s About:

Nadia Turner is in her last year of high school and grieving the death of her mother when she begins secretly dating Luke Sheppard, a twenty-one year-old former football player whose injury has left him waiting tables at a diner. Their short-lived and complicated romance impacts both of them well into adulthood.

Why Past Me Should Read It:

This haunting and lyrical novel is told from multiple perspectives, including Nadia’s and Luke’s. On the surface, Luke seems like a textbook cad. However, the author takes us beyond Luke’s exterior and shows us the reason for his behavior. Rather than relying on stereotypes, Bennett presents us with a fully-formed human with his own motives and regrets. This book would remind me that everyone is more complex than their worst moments.

We Should All Be Feminists by Chimamanda Ngozi Adichie

What It’s About:

Adichie’s essay, based on her Tedx talk of the same name, explores feminism in a simple and conversational manner. She describes the chauvinism she has experienced and provides straightforward anecdotes of sexism to which many of us can identify.

Why Past Me Should Read It:

A cad, by definition, acts dishonorably toward women. Nobody needs that. Adichie’s slim book would be a reminder that I can do better.

 

The One Who Broke My Heart  

Hyperbole and a Half: Unfortunate Situations, Flawed Coping Mechanisms, Mayhem, and Other Things That Happened by Allie Brosh

What It’s About:

Based on Brosh’s hilarious blog, the book is a compilation of drawings and stories of Brosh’s weirdness as a child, her odd dogs, and her struggles with anxiety and depression.

Why Past Me Should Read It:

This isn’t a book about heartbreak. However, one of the worst parts of going through a breakup is feeling isolated. You can’t talk to the person that used to be one of your closest friends. Sometimes, the two of you had mutual friends and you’re not sure how to talk to them anymore. Brosh’s book is so emotionally honest and funny, it’s hard to feel alone while you’re reading it. Anyone who’s ever felt like the “weird one” in a social situation- or who has battled depression or anxiety- will relate to Brosh’s stories.  

Tiny Beautiful Things: Advice on Love & Life from Dear Sugar by Cheryl Strayed

What It’s About:

The compilation of Strayed’s once-anonymous advice column from The Rumpus website provides wise and empowering advice on everything from sex to relationships to pursuing your dreams.

Why Past Me Should Read It:

Reading this book is like spending the evening with your empathetic but unflinchingly honest best friend. And Strayed’s no-bullshit approach would really have resonated at a time when I felt like everyone had it together except me.

An Untamed State by Roxane Gay

What It’s About:

Mireille is visiting her parents in Haiti with her husband and infant son when she’s kidnapped in front of her father’s Port-Au-Prince estate in broad daylight by a gang of heavily armed men. As it becomes clear her father intends to resist the kidnappers, Mireille must endure the torments of a man who resents everything she represents. An Untamed State tells the story of Mireille’s thirteen days in captivity, as well as her subsequent struggle to regain her sense of self.

Why Past Me Should Read It:

After my first heartbreak, I desperately needed to get out of my own head. I was too focused on my unfolding personal drama. An Untamed State is the kind of novel that will transport you from wherever you are into Mireille’s world. This powerful story of devastation and redemption will also put into perspective any typical romantic quarterlife crisis.

 

The One Whose Heart I Broke 

The Missing Piece Meets the Big O by Shel Silverstein

What It’s About:

The Missing Piece is a triangle who is searching for the piece that will complete him. Some pieces are too small, some are too large. One fits at first until the Missing Piece begins to outgrow him. Eventually, the Missing Piece meets the Big O, who teaches him that no other pieces are required.

Why Past Me Should Read It: 

Breaking up with someone often comes with so much guilt. It’s terrible to know that you’ve hurt someone. In my twenties, I would sometimes try to make a relationship work well past the point when I knew I was unhappy. This book serves as a reminder that sometimes, in order to be whole, we have to roll on our own.

Written on the Body by Jeanette Winterson

Written on the Body by Jeanette Winterson cover

What It’s About:

This all-consuming novel explores the passionate highs and devastating lows of being in love. The narrator, who has neither name nor gender, chronicles an affair with Louise, an unhappily married woman with a terrible secret. The story is a cathartic meditation on love lost.

Why Past Me Should Read It: 

This book more fully encompasses an obsessive love affair better than any other story I’ve ever read. I’m not saying that level of intensity is sustainable or even always desirable. But when I was hanging onto lackluster relationships because I couldn’t muster the energy to end them, this book would have made me say, “Okay- that. I need to feel more of that in my life.”

 

The Mutually Assured Destruction

Gone Girl by Gillian Flynn

What It’s About:

Amy and Nick are preparing to celebrate their fifth wedding anniversary when Amy disappears. Mired in lies and deceit, Nick is the obvious suspect. But Amy’s diary reveals a woman more complicated than she initially seemed. This book (and the subsequent movie) have been everywhere over the last few years- for good reason.

Why Past Me Should Read It: 

Sometimes you break someone’s heart. Sometimes you get your heart broken. And sometimes, you find yourself caught in a twisted, dysfunctional dance with someone you think you might have liked at some point. Typically considered a psychological thriller, this is also a cathartic read for anyone who’s a disaster- and has recently gotten out of a relationship with a fellow hot mess.

Zelda: A Biography by Nancy Milford

What It’s About:

Zelda Sayre Fitzgerald, best known as wife and muse to F. Scott Fitzgerald, was an author and artist in her own right. Zelda was passionate and rebellious- the flapper who symbolized the roaring twenties. Her desire to be creative often conflicted with F. Scott’s appropriation of their lives for his work. Milford masterfully portrays their booze-y, tumultuous relationship.

Why Past Me Should Read It: 

F. Scott and Zelda seemed to really love it each other. Regardless, they often weren’t very good for one another- the quintessential “mutually assured destruction” couple. In my twenties, I romanticized the idea of tempestuous relationships among artists. This book shows the toll her marriage took on Zelda

Trainwreck: The Women We Love to Hate, Mock, Fear And Why by Sady Doyle


What It’s About:

She’s everywhere once you start looking for her: the trainwreck. She’s Britney Spears shaving her head, Whitney Houston saying, “crack is whack,” and Amy Winehouse, dying in front of millions. But the trainwreck is also as old (and as meaningful) as feminism itself.

From Mary Wollstonecraft—who, for decades after her death, was more famous for her illegitimate child and suicide attempts than for A Vindication of the Rights of Woman—to Charlotte Brontë, Billie Holiday, Sylvia Plath, and even Hillary Clinton, Sady Doyle’s Trainwreck dissects a centuries-old phenomenon and asks what it means now, in a time when we have unprecedented access to celebrities and civilians alike, and when women are pushing harder than ever against the boundaries of what it means to “behave.”

Why Past Me Should Read It:

There’s no shortage of people/media sources/comment sections ready to label a woman crazy- especially those of us who feel things strongly, struggle with addiction, or behave outrageously in public.  Many of us subconsciously internalize the message that we’re somehow irrevocably damaged. Doyle’s funny and insightful book gives us a social and historical context for our society’s need to provoke, witness, and condemn women for their behavior.

 

The Happily Ever After

Quiet: The Power of Introverts in a World That Can’t Stop Talking by Susan Cain

quiet susan cain

What It’s About:

In Quiet, Susan Cain argues that society undervalues introverts and shows how much we lose in doing so. She charts the rise of the Extrovert Ideal throughout the twentieth century and explores how deeply it has come to permeate our culture. She also introduces us to successful introverts—from a witty public speaker who recharges in solitude after his talks, to a record-breaking salesman who quietly taps into the power of questions. Passionately argued, superbly researched, and filled with indelible stories of real people, Quiet has the power to permanently change how we see introverts and, equally important, how they see themselves.

Why Past Me Should Read It:

This book was released when my now-husband and I had been dating for about six months. I was serious about him and I had never been so happy. But there was one consistent issue that bothered me. After a long and frustrating day, he wanted to go out and unwind with friends. Meanwhile, all I wanted to do was sit in my pajamas, each carbs, and watch Jeopardy! This doesn’t sound like a big deal, but I sometimes wondered if this fundamental difference would divide us: Was I too antisocial to fit into his life well? And what was the deal with his constant drive to be around other people? Reading Cain’s book was a serious aha! moment for me. It helped me realize that he gets the same sense of catharsis out of socializing that I do from pizza and Alex Trebek. We’re going for the same physiological response, but our bodies have different ways of getting there. That realization helped us tremendously- we found it much easier to encourage one another’s versions of self-care.

The Year of Yes by Shonda Rhimes

What It’s About: 

Grey’s Anatomy. Scandal. How to Get Away with Murder. Shonda Rhimes is a creative force who has had an enormous impact on the entertainment industry over the decade. This book explores the impact of a decision Rhimes made when, over Thanksgiving dinner, her sister muttered something that was both a wake up and a call to arms: You never say yes to anything. Shonda knew she had to embrace the challenge: for one year, she would say YES to everything that scared her.

This poignant, intimate, and hilarious memoir explores Shonda’s life before her Year of Yes—from her nerdy, book-loving childhood to her devotion to creating television characters who reflected the world she saw around her. The book chronicles her life after her Year of Yes had begun—when Shonda forced herself out of the house and onto the stage; when she learned to explore, empower, applaud, and love her truest self. Yes.

Why Past Me Should Read It: 

This book is a good balance to Quiet. While self-care in any form is a necessity, so is occasionally moving out of your comfort zone. My husband is really good at saying yes to novel experiences- and getting me to do so as well. With his encouragement, I’ve challenged myself by moving across the country, hiking a cloud forest in Panama, and reading my middle school journals in front of 500 strangers at a Mortified performance. After years of learning to take care of myself by saying no: To the wrong boys, bad choices, and self-doubt, it’s important to remember when to say yes.

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