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About The Book

The “brilliantly wry” (Lena Dunham) and “lovably awkward” (Mindy Kaling) New York Times bestseller from the creator of HBO’s Insecure.

In this universally accessible New York Times bestseller named for her wildly popular web series, Issa Rae—“a singular voice with the verve and vivacity of uncorked champagne” (Kirkus Reviews)—waxes humorously on what it’s like to be unabashedly awkward in a world that regards introverts as hapless misfits and black as cool.

I’m awkward—and black. Someone once told me those were the two worst things anyone could be. That someone was right. Where do I start?

Being an introvert (as well as “funny,” according to the Los Angeles Times) in a world that glorifies cool isn’t easy. But when Issa Rae, the creator of the Shorty Award-winning hit series The Misadventures of Awkward Black Girl, is that introvert—whether she’s navigating love, the workplace, friendships, or “rapping”—it sure is entertaining. Now, in this New York Times bestselling debut collection written in her witty and self-deprecating voice, Rae covers everything from cybersexing in the early days of the Internet to deflecting unsolicited comments on weight gain, from navigating the perils of eating out alone and public displays of affection to learning to accept yourself—natural hair and all.

The Misadventures of Awkward Black Girl is a book no one—awkward or cool, black, white, or other—will want to miss.

Reading Group Guide

This reading group guide for The Misadventures of Awkward Black Girl includes an introduction, discussion questions, and ideas for enhancing your book club. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.



Issa Rae has never felt comfortable in the middle of a Save the Last Dance–style circle. She’s always worn the wrong pants, kissed the wrong boy, felt the wrong way, or simply been the wrong girl. The Misadventures of Awkward Black Girl is a dazzling collection of essays about growing up learning to love the things in your life that make it unique, even when those things also make it mighty awkward. She writes about being a black girl who just can’t dance, about being unhappy working in a cubicle as her Web series was taking off, about (not) arriving at a personal fashion sense, about the difficulty of her parents’ divorce, and about finding and losing love, again and again. Throughout the book, Rae is honest, insightful, and laugh-out-loud funny—and of course, arrestingly awkward.


Questions and Topics for Discussion

1. Rae writes candidly about her family in nearly all of her essays. How does she use humor to write about very private family stories in a very public way?

2. The anonymity of the internet, particularly in its early days, when it was difficult to upload pictures and find out who was friends with whom, allowed Issa to project a personality different from her own. Was that the internet’s “age of innocence,” or the beginning of so many troubles we now associate with hook up culture?

3. Like so many, Issa struggles with weight, sometimes putting on thirty pounds more than what she deems optimal. After successfully completing the Master Cleanse she writes, "once the compliments come in, you're totally seduced into equating self-worth with skinniness. . . .The compliments were the most addictive drug of all." Can you relate? Do you, too, "live for that validation that accompanies weight loss"?

4. Issa writes amusingly of the apprehension she felt as a young girl when she thought she might be expected to fulfill stereotypes associated with being black: to either know the latest hit rap lyrics by heart or to be able to dance like she came straight from a video shoot. She felt as if she were expected to “put my hands on my knees, pop my booty, and do the Tootsie Roll.”  How does she use humor to deflect the anxiety? What stereotypes have people projected onto you, and how do you deflect their assumptions?

5. Race is a central issue in the book, but Rae describes her frustration at people who make it a central point in their lives. How does she walk this line herself in the book?

6. In "Leading Lady," Rae writes, "You could say I have an entertainment complex. It stems from growing up during the golden age of nineties television. I look back and realize what a huge and amazing influence it was to have an array of diverse options to watch almost every night of the week." She then laments how the subsequent decade offered fewer options. What about now? Are our choices more diverse? Does the internet, with YouTube and the like, level the playing field in a substantive way?

7. The Misadventures of Awkward Black Girl is about learning to accept yourself. In Rae’s case she had to accept that she was typically the most awkward girl in the room. How did being an introvert limit her? If you are an introvert, how does it limit you? Is the world easier for extroverts?

8. How is Rae’s life and artistry unique to the internet age?

9. Is it okay to use humor to talk about difficult subjects? Are there any taboo subjects, i.e. those that simply can't be approached with anything approaching humor or satire?

10. In "The Struggle" Rae writes, “I love being black; that's not a problem. The problem is that I don't want to always talk about it. . . ." Does being a card-carrying member of one group mean you always have to represent that group in public? What group do you represent, and are you expected to always speak for that group? (Gay, Asian, single mom, Latin, trust-fund baby, Jewish, geek, metrosexual, big girls, skinny girls, for example).

11. The topic of infidelity is a difficult one to approach with cool-headed nuance. How does Rae come to terms with this difficult topic in her life?

12. In what ways does Issa’s unique background—half African, half African-American, one half of her childhood spent on the East Coast, the other on the West Coast—position her to see the world in a unique way? If your life is also composed of interesting cultures, how has your perspective on life been influenced? Is it empowering? Or more fractious?



1. Watch a few episodes of The Misadventures of Awkward Black Girl on YouTube and pick a character who you think has been inspired by a person from Rae’s book. How is that person’s depiction different on-screen and on the page?

2. Describe times in your life when you, too, have felt awkward. Do you think it is something you outgrow or something that is a part of you? How does Rae see her own awkwardness?

3. Pretend you have to write an intimate essay about one of the most difficult parts of your life. What do you think would be the obstacles in writing about this topic? Would making the essay funny help you deal with some of those issues or would it exacerbate them?

About The Author

Photograph by Kat Contreras

With her own unique flare and infectious sense of humor, Issa Rae’s content has garnered more than twenty-five million views and more than 200,000 subscribers on YouTube. In addition to making the Forbes “30 Under 30” list twice and winning the 2012 Shorty Award for Best Web Show for her hit series The Misadventures of Awkward Black Girl, Issa Rae has worked on web content for Pharrell Williams, Tracey Edmonds, and numerous others. She developed a TV series with Shonda Rhimes for ABC and is currently developing a half-hour comedy, Insecure, for HBO. Issa has received national attention with major media outlets including The New York Times, CNN, Elle, Seventeen, Rolling Stone, VIBE, Fast Company, MSNBC, Essence, and more.

Product Details

  • Publisher: 37 Ink (February 10, 2015)
  • Length: 224 pages
  • ISBN13: 9781476749099

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Raves and Reviews

"With MISADVENTURES OF AWKWARD BLACK GIRL, Issa shows us why she is the queen of media and why we need a multiplicity of voices in the media."

– Los Angeles Times

"Issa Rae nailed it: Her book TheMisadventures of Awkward Black Girl is why the term must-read exists."

– Marie Claire

"A book ripe with insights for the awkwardamong us."

– Cosmo

“For fans of Mindy Kaling’s Is EveryoneHanging Out without Me?. . . ). Already a strong voice for diversity in the media, Rae issomeone readers of all stripes will love getting to know, however awkwardly.”

– Booklist

“In Rae, her audience has landed on a singular voicewith the verve and veracity of uncorked champagne. An authentic and freshextension of the author's successful Web series.”

– Kirkus Reviews

“You'll laugh freakishly hard over the geniusYouTube star's book about everything from PDA to coworkers who always suck up”

– Glamour

“Delightfully deadpan…the real discovery here is that Rae has a natural flair for narrative,showing promise as an essayist with her unique perspective…a writer to watch.”

– Essence

Cutting, laugh out loud observations.”

– Uptown Magazine

“I loved this book. Issa Rae is brilliant, funny andloveably awkward.”

– Mindy Kaling

"Ifyou like Awkward and love Black. Or love Awkward and like Black. Or if you'relike me and just can't get enough of Awkward and Black in equal doses, then youwill love love love Issa Rae and her Awkward Black Girl tales of Awkward BlackGirlishness. That wasn't too awkward was it?"

– Larry Wilmore

“In her hilarious debut book, Issa Rae uses the brilliantly wry voice she's honed in her searing and necessary webseries to tell a story that is so personal yet so universal: awkward girl becomes awkward woman, and in doing so realizes that awkward is the best way to be.”

– Lena Dunham

"Farfrom awkward, Issa Rae wittily shows us how to navigate a society stillobsessed with stereotypes. Her essays are a rallying cry for all those daringto be unique, international, and fully human. A must read for thinking andfeeling people from 8 to 80."

– Susan Fales-Hill

Awards and Honors

  • Topaz Nonfiction Reading List (TX)

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