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5 Messy Characters You Can’t Help But Love

Zeniya Cooley Headshot
September 13 2022
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One of my guilty pleasures is reading about messy characters—and boy, do I have a list below! These five women make questionable and controversial decisions, yes, but they’re also navigating a strange world that doesn’t always welcome them with open arms. On their quests for meaningful lives, they stumble and stagger. But that’s the beauty of this human experience: we’re lurching forward in life and learning as we go, so mistakes are inevitable. At least, that’s what I’ve found with the fascinating characters in this list.

I encourage you to get to know these women. You’re probably not crushing on someone you shouldn’t like Feyi or seeking healing with a few oddballs in New Mexico like Mona. Even if you are, I’m not judging! But you might learn something from these characters: that grief is ever evolving, that healing is not so wholesome. So get comfy with these at times uncomfortable protagonists. They’re perfectly imperfect—just like us.

Queenie
by Candice Carty-Williams

Fans of I May Destroy You find another brave heroine in Queenie Jenkins, a Jamaican British woman in a spiral. While rebounding from a breakup with her white boyfriend, she gets mired in a few sticky situationships, including an entanglement with a colleague at her newspaper job. As I read this book, I couldn’t help but empathize with Queenie and her misadventures. She might not be a mirror image of me and other women navigating the tumult of our twenties, but we can all find shards of ourselves in this character’s sinuous journey to self-discovery.

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Queenie
Candice Carty-Williams

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People Person
by Candice Carty-Williams

As a social media addict, how could I not relate to aspiring lifestyle influencer Dimple Pennington? She’s the middle child of her roving father’s five adult children—all of whom she barely knows. But like many of us, Dimple is more concerned with impressing the people that follow her online. That is, until a dramatic event reunites the Pennington children with their gallivanting patriarch. Ultimately, Dimple and her siblings realize they might have issues, daddy- and device-related, but they also have each other. What’s more reassuring than that?

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People Person
Candice Carty-Williams

The author of the “brazenly hilarious, tell-it-like-it-is first novel” (Oprah Daily) Queenie returns with another witty and insightful novel about the power of family—even when they seem like strangers.

If you could choose your family...you wouldn’t choose the Penningtons.

Dimple Pennington knows of her half siblings, but she doesn’t really know them. Five people who don’t have anything in common except for faint memories of being driven through Brixton in their dad’s gold jeep, and some pretty complex abandonment issues. Dimple has bigger things to think about.

She’s thirty, and her life isn’t really going anywhere. An aspiring lifestyle influencer with a terrible and wayward boyfriend, Dimple’s life has shrunk to the size of a phone screen. And despite a small but loyal following, she’s never felt more alone in her life. That is, until a dramatic event brings her half siblings Nikisha, Danny, Lizzie, and Prynce crashing back into her life. And when they’re all forced to reconnect with Cyril Pennington, the absent father they never really knew, things get even more complicated.

From an author with “a flair for storytelling that appears effortlessly authentic” (Time), People Person is a vibrant and charming celebration of discovering family as an adult.

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You Made a Fool of Death with Your Beauty
by Akwaeke Emezi

I was rooting for this novel’s heroine, Feyi Adekola, an artist reentering the dating scene five years after the death of her husband. Following a rooftop hookup with one guy and a steamy stare-down with that guy’s close friend, Feyi finds herself opening up to Nasir, the perfect person to love after all the grief she’s known. But things get tricky when she starts falling for the person you’d least expect. Emezi’s book isn’t so much about who Feyi chooses but what she chooses: a second chance at love and a life after loss.  

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You Made a Fool of Death with Your Beauty
Akwaeke Emezi

A New York Times bestselling author, National Book Award finalist, and “one of our greatest living writers” (Shondaland) reimagines the love story in this fresh and seductive novel about a young woman seeking joy while healing from loss.

Feyi Adekola wants to learn how to be alive again.

It’s been five years since the accident that killed the love of her life and she’s almost a new person now—an artist with her own studio, and sharing a brownstone apartment with her ride-or-die best friend, Joy, who insists it’s time for Feyi to ease back into the dating scene. Feyi isn’t ready for anything serious, but a steamy encounter at a rooftop party cascades into a whirlwind summer she could have never imagined: a luxury trip to a tropical island, decadent meals in the glamorous home of a celebrity chef, and a major curator who wants to launch her art career.

She’s even started dating the perfect guy, but their new relationship might be sabotaged before it has a chance by the dangerous thrill Feyi feels every time she locks eyes with the one person in the house who is most definitely off-limits. This new life she asked for just got a lot more complicated, and Feyi must begin her search for real answers. Who is she ready to become? Can she release her past and honor her grief while still embracing her future? And, of course, there’s the biggest question of all—how far is she willing to go for a second chance at love? ​

Akwaeke Emezi’s vivid and passionate writing takes us deep into a world of possibility and healing, and the constant bravery of choosing love against all odds.

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Pretend I'm Dead
by Jen Beagin

I relished the bohemian charm of Jen Beagin’s debut novel about a twentysomething adrift in Massachusetts. Mona, a cleaning lady, gets by with rubber gloves, but her life takes a chaotic turn when she meets a heroin addict at a needle exchange program. She falls dangerously in love with him, and in her attempt to heal from old and new traumas decamps to New Mexico. The eccentrics she encounters in this new world teach her valuable lessons. However, the biggest lesson of all, self-acceptance, is one she will have to learn on her own.

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Pretend I'm Dead
Jen Beagin

NAMED A BEST BOOK of the YEAR by O, THE OPRAH MAGAZINE, REFINERY 29, and KIRKUS REVIEWS
SHORTLISTED FOR THE CENTER FOR FICTION FIRST NOVEL PRIZE

A “wondrous,” (O, The Oprah Magazine) “scathingly funny” (Entertainment Weekly) debut from Whiting Award winner Jen Beagin about a cleaning lady named Mona and her quest for self-acceptance and belonging after her relationship with a loveable junkie goes awry.

Jen Beagin’s funny, moving, fearless debut novel introduces an unforgettable character, Mona—almost twenty-four, emotionally adrift, and cleaning houses to get by. Handing out clean needles to drug addicts, she falls for a recipient she calls Mr. Disgusting, who proceeds to break her heart in unimaginable ways.

Seeking a kind of healing, she decamps to Taos, New Mexico, for a fresh start, where she finds a community of seekers and cast-offs, all of whom have one or two things to teach her—the pajama-wearing, blissed-out New Agers, the slightly creepy client with peculiar tastes in controlled substances, the psychic who might really be psychic. But always lurking just beneath the surface are her memories of growing up in a chaotic, destructive family from which she’s trying to disentangle herself, and the larger legacy of the past she left behind.

The story of Mona’s quest for self-acceptance in this working class American world is at once hilarious and wonderfully strange, true to life and boldly human, and introduces a stunning, one-of-a-kind new voice in American fiction.

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The Roxy Letters
by Mary Pauline Lowry

Bridget Jones has a millennial successor in Roxy, who writes aggrieved letters to her ex-boyfriend and roommate, Everette. Working as a deli maid at Whole Foods, Roxy grows more dissatisfied with the corporatization of her beloved Austin. The last straw comes with the arrival of a new Lululemon, but confronting a rapidly changing city forces Roxy to examine her own life. So she writes about it all: her failed flirting attempts, her unglamorous work, and even her new purchase from the same loathsome Lululemon that replaced her favorite video rental store. That’s the thing about Roxy. She’s flawed and full of contradictions—but aren’t we all?

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The Roxy Letters
Mary Pauline Lowry

Meet Roxy. For fans of Where’d You Go, Bernadette and Bridget Jones’s Diary comes “just the kind of comic novel we need right now” (The Washington Post) about an Austin artist trying to figure out her life one letter to her ex-boyfriend at a time.

Bridget Jones penned a diary; Roxy writes letters. Specifically: she writes letters to her hapless, rent-avoidant ex-boyfriend—and current roommate—Everett. This charming and funny twenty-something is under-employed (and under-romanced), and she’s decidedly fed up with the indignities she endures as a deli maid at Whole Foods (the original), and the dismaying speed at which her beloved Austin is becoming corporatized. When a new Lululemon pops up at the intersection of Sixth and Lamar where the old Waterloo Video used to be, Roxy can stay silent no longer.

As her letters to Everett become less about overdue rent and more about the state of her life, Roxy realizes she’s ready to be the heroine of her own story. She decides to team up with her two best friends to save Austin—and rescue Roxy’s love life—in whatever way they can. But can this spunky, unforgettable millennial keep Austin weird, avoid arrest, and find romance—and even creative inspiration—in the process?

With timely themes and hilarious, laugh-out-loud moments, Roxy Letters is a smart and clever story that is “bursting with originality, quirky wit, and delightful charm” (Hannah Orenstein, author of Playing with Matches).

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Photo credit: Off the Shelf

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