The Misadventures of Awkward Black Girl

The Misadventures of Awkward Black Girl

by Issa Rae
The Misadventures of Awkward Black Girl

The Misadventures of Awkward Black Girl

by Issa Rae


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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.

Product Details

ISBN-13: 9781476749075
Publisher: Simon & Schuster
Publication date: 07/12/2016
Series: A Bestselling Memoir
Edition description: Reprint
Pages: 224
Sales rank: 118,027
Product dimensions: 5.50(w) x 8.30(h) x 0.60(d)

About the Author

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.

Read an Excerpt

The Misadventures of Awkward Black Girl

At only eleven years of age, I was a cyber ho. Looking back, I’m embarrassed. For me. For my parents. But oddly enough, my cyber social debauchery is indirectly correlated with my current status as a so-called internet pioneer. It all started when I began catfishing—creating characters and transmitting them over the internet—though back then people just called it “lying.” Had my father not signed my entire family up with America Online ­accounts for the computer in our modest Potomac, Maryland, home I don’t know that I’d have had the tools to exploit the early ages of the internet.

Two years earlier, my oldest brother, Amadou, had gone away to college at Morehouse, freeing up the coveted computer, which was housed in the basement, for my use. Before he decamped for college, I would spend hours at a time watching him type the commands into MS-DOS that would transport us to the magical kingdom of Sierra’s King’s Quest VI on our IBM. I never had a strong desire to play the game myself—I always assumed I wasn’t smart enough to play it on my own—until Amadou graduated from the house and I no longer had anyone to excitedly observe. I looked up to my oldest brother as the epitome of intelligence. He knew everything, though he was too humble to be ostentatious with his knowledge as I would have been had I been as smart. So I simply observed. At eighteen, he was an official adult, and he had a duty to selflessly spread his intelligence to the world, other people’s younger sisters included. His absence left a void in my heart and in the basement, particularly where the use of the computer was concerned.

I wasn’t next in line for the computer, but my second-oldest brother, Malick, was too preoccupied with football, girls, and high school to care. He’d occasionally make use of it for term papers and Tetris, but otherwise, it was mine for the taking. Using the computer wasn’t foreign to me, by any means. I had an old Apple computer in my very own room (a double source of jealousy for my younger brother), where I played Number Munchers and self-published my stories on perforated paper from an excruciatingly noisy printer.

“Jo-Issa, are you wasting paper again?!” my mother would yell from her makeshift home office, tipped off by the mechanical snitch. When alone, and mom-approved, I actually loved to hear the robotic crunching and whirring that the printer made while laying to ink my very own written words. But the computer in my room paled in comparison to the one downstairs, in the basement. For one thing, the large floppy disks—I think they were actually called hard disks, what the f%4# 90s?—were becoming extinct, and rightfully so, since the data on those things could be lost with the smudge of a finger. And since my computer took only the “hard” disks, my game choices were limited to nerdy learning games and text-based adventure games with no visuals. BLECH. BORING. BOO.

The other reason my computer wasn’t a huge triumph for my preteen self-discovery was because it lacked a modem, which meant no dial-up internet for me. But AOL changed my life. Specifically, it changed my social life. To be more precise: AOL gave me a social life. It ignited my social development and expanded my concept of sexuality. Because of AOL, I had imaginary friends that weren’t imaginary. I had elaborate conversations devoid of awkward silences. And, perhaps most valuable of all, I could actually talk to boys. At my command!

Before my parents caught wind of frightening news reports of child predators, I spent my days and after-school evenings in chat rooms, learning to speed read, talking to kids my age who were also ahead of the curve. Or pedophiles, who were remarkably creative and persistent in their forbidden pursuit. Pedos actually had it made in the mid-nineties, before the media exposed them. Talk about the glory days.

My friends at school, other fifth graders, didn’t seem to relate when I mentioned “chat rooms” and “profiles” or when I sang along to the dial-up internet song I made up in my head. It seemed that, for a brief moment, only I was privy to this alternate American universe that lived online.

By the time my family moved to Los Angeles to join my dad, a pediatrician, who had seized an opportunity to open his own family clinic there, my relationship with the computer had grown immensely, much to the dismay and irritation of my mother.

“You’re always on the computer! Go do your homework.”

“I already finished.”

“Well then, go outside and play!”

She just didn’t get it. Only recently, in my late twenties, did she come to realize that my excessive computer use is what led me to becoming the self-employed, almost-focused career woman I am today.

By the summer of 1996, more of my friends from Maryland had adopted AOL. It helped us bridge the three thousand miles between us. By then, I was already over the handwritten letters of yesteryear. That was a form of communication of the third world, reserved for pen pals from Ghana and Spain. Besides, the “You’ve Got Mail” greeting was way more exciting than the dead silence of receiving a letter. Exclaiming, “I’ve got mail!” in the foyer to yourself isn’t the same—trust me.

It was through electronic mail that I’d tell my friends back home about my Hollywood adventures. Never mind the fact that I lived in Windsor Hills, thirty minutes away from Hollywood, and that I was struggling to make friends. Or that my sense of style was horrendous, and my middle school had done away with lockers so the authorities could better monitor drug use. ALL I EVER WANTED WAS A LOCKER! I felt robbed of the middle school experience I saw on Boy Meets World and Doug, but my friends didn’t have to know that. I led them to believe I was on the brink of stardom, just by breathing in the recycled smog of other celebrities around me. Plus, I lived down the street from Ray Charles’s old house. I was famous by association.

Our move back to Los Angeles also fulfilled a dream I’d held on to for five whole years: we were finally reunited with my father. He’d visit us in Maryland once every two to three months for an extended period of time, but for the most part, I spent my elementary school years without him and, in his absence, had constructed a superheroic, Arnold Schwarzenegger-esque Father of the Year image of him in my mind. My dad was the man, and whenever I’d tell my teachers my father was a doctor who was too busy to come to Back to School night, their surprised and delighted “Oh!” always gave me a sense of pride. I didn’t speculate then that they were making an assumption about my family’s income and placing my blackness into a Huxtable category. To me, their reaction implied that a doctor was an important profession, which meant my dad was important. And I wanted to be just like my dad.

I so longed to live with him and see my family complete, I neglected to figure out that the reunion meant double supervision. The only computer in the house was in my dad’s home office, and now internet activity was being monitored without my knowing it. Going through puberty during the dawn of the internet could have left me unscathed if my dad weren’t so annoyingly tech savvy. If only he, a native African, were like the tribal stereotypes I read about in my middle school history books, I would have gotten away with so much more. Instead, I found myself sneaking to look up “sex” in the encyclopedia and then cross-referencing my findings with the search results. Also, unbeknownst to me, my dad had added a kid-safe image blocker, so I was always limited to boring text-only definitions.

I was wrought with hormones and obsessed with finding a boyfriend. All I knew was that boys cared about sex and I didn’t know enough about it. I was too embarrassed to ask my peers. They were already über-judgmental about my naïveté to all things black after I accidentally exposed myself when Tupac died. “Two-pack died? What did he sing?”

Normally, I would have been spared from middle school humiliation by asking my two older brothers directly. They would have happily explained who Tupac was and I would have happily plagiarized their responses and relayed their feelings about him as my own. But my second-oldest brother had by then also graduated from the house to go to college and I was left as the oldest in the house. If I had trouble attracting the boys at my school before, my ignorance about Tupac destroyed any remote chance I might have had.

All I knew was that I had all these developing feelings for boys and that I wanted desperately for them to notice me. They did, but for reasons that didn’t help my quest: my nap-tural hair; my underdeveloped, seemingly concave breasts; my white-girl accent, and my tomboyish appearance. The prototype of lust for the boys my age was a light-skinned girl with long hair, and I just didn’t fit that profile. But I didn’t want to believe that. So I would imagine instead that I held the interest of all the boys and often convinced myself of that. All the while, I remained the continued object of disdain from my peers. I often found myself emboldened whenever a guy would show me any attention at all, i.e. “Ay, you did the homework? Let me copy,” or “You got ten cents for the vending machine?” I blame any misread social cues on Saved by the Bell. Zack and Kelly’s romance was something I wanted so badly to emulate.

My first-ever junior high school dance was approaching and, with the help of a Saturday morning marathon of Saved, I built up the courage that Monday morning to talk to Remington, an eighth-grade-looking sixth-grader who I’m pretty sure had been held back (though nobody talked about it). He had thick facial hair and muscular, athletic arms. He loved women, and frequently expressed his sexual desires in a way that hinted at experience. In my eyes, he was the answer. And I had so many questions. One of them, I worked up the courage to ask in front of his friends. I approached him right after our Environmental Studies class was dismissed, casually, waiting for him to pick up his only school supply, a single folder.

“Hey, Remington,” I started, shyly. “Are you going to the dance?”

He didn’t miss a beat: “Not with you!”

His friends didn’t even try to hide their laughter. Not a single one. I smiled and tried to play it off.

“Oh. No—I didn’t mean that. You thought I was asking for me?”

But it was too late; they had already pushed past to leave me in the classroom alone, my Environmental Studies teacher avoiding eye contact with me.

Ever optimistic, I went to the dance by myself, with the hope that maybe a boy there would ask me to dance. Maybe it would be Quentin, the skinny, half-albino/half-effeminate boy to whom I’d been sending “secret admirer” letters. It was the least he could do, after excitedly exposing to the class that I had been writing him love notes for weeks. Despite my humiliation, I couldn’t really blame him. It happened naturally enough. The homeroom teacher brought up “secret admirers” in her announcement about Valentine’s Day grams.

“Does anyone know what a ‘secret admirer’ is?” she asked.

“I do! I do, Ms. Nash!”

My heart plummeted to my stomach as I noticed him anxiously looking in my direction.

“What do you know about secret admirers, Quentin?” asked Ms. Nash.

“That girl right there was writing me ‘secret admirer’ notes.” He smiled at me, as if his public acknowledgment didn’t violate the very purpose of the “secret” in “secret admirer.”

Surely, he would save me from walking around the junior high dance all alone, in the jean jumper and white turtleneck I had packed in my backpack just for this after-school occasion. (I never wore dresses.) Somebody had to take notice and ask me to dance, based on that alone. Unfortunately, no one ever asked.

I was rapidly coming to the conclusion that boys didn’t find me attractive. That was heartbreaking. My self-esteem was in danger and had it not been for the saving grace of the Instant Message feature on AOL, I probably would have suffered death by trying too hard.

I don’t remember the first time I typed to a stranger. It wasn’t monumental for me. But it did speak to a desire to escape myself. For one thing, I could be anyone I wanted to be online. With each swift keystroke, a new, fearless identity emerged. I could be light-skinned with long hair, or blue-eyed with blond hair. Or experienced, witty, and seductive—things nobody saw me as in real life. I could be anyone’s type and was able to do so because during the early stages of AOL, pictures were pretty rare, though around the time that IMs came along, home scanners were growing more popular. Thankfully, however, pictures took forever to upload and weren’t in high demand, so people were content with self-descriptions. As people tended to be quite generous in their descriptions of themselves, I figured I could be, too. What did it matter?

“A/S/L,” the pop-up conversation would start.

Age/Sex/Location? (This blatant acronym had to have been tooled by pedophiles. The genius!) There was something flattering about being selected out of a pool of thirty to sixty people in a chat room for a private talk. I’d imagine it was like being chosen at a party to dance, though I wouldn’t know anything about that. But for my chameleon-esque purposes, responding to this conversation opener was the hardest part. I couldn’t become a type if I didn’t know what I was working with. If I were in the mood to talk to someone my age, I’d be honest.

“11/F/Cali, u?”

“13/f/az. hi.”

Trick, I don’t want no friends right now! On to the next. Sometimes I’d be the pursuer. I’d visit the R&B, Rap, or Games chat rooms and scout screen names that would give me hints at my preferred types: soccrplaya83, muscleman39, blkboy17. All I had were snippets of open chats to go by. What were they contributing to the larger public conversation? I couldn’t choose someone who was too active in the chat room; his chances of committing to a one-on-one were slim. Besides, someone who revels in being the center of attention is not my type. I don’t like to compete. Instead, I went for those who would contribute a few meaningful phrases here and there: “games are cool” or “yah i love r. kelly.” Subtle hints like those were enough to provoke me to reach out.

I’d begin:

SuGaLuv112: “hi. a/s/l?”

muscleman39: “18/m/de. u??”

SuGaLuv112: “17/f/cali.”

muscleman39: “cool, what’s up?”

SuGaLuv112: “nothin. chillin. bored.”

muscleman39: “are you horny?”

What? Like rhinos? My knowledge of internet slang was coming up empty. But I tried.

SuGaLuv112: “what do u you mean?”

Then came the door-slam sound effect from my computer speakers.

muscleman39 has signed off.

After a couple of weeks, and some more of these incidents, I decided to finally look up the definition of “horny.” What was being asked of me? My Encarta CD-ROM produced no answers, but Yahoo was full of them.

hor-ny (hôr ne): desiring of sexual activity.

Oh my freaking God. Of course. YES! That’s exactly what I was. The answer to what I was looking for in so many ways was being dangled before me, and all I had to do was respond with a simple “yes.” I couldn’t wait for the next opportunity to showcase my new personality trait. I sought it, thirstily. This time ready for the exchange and wealth of knowledge that would follow. I was so appropriately excited and ready.

My first online relationship started off innocently enough. Every day after school, around three thirty, I would log on. It was the perfect time. My mom, who was too tired to worry about her remaining three kids, after dealing with one hundred plus of her French students, would go take a nap. During that time, nobody could go in and disturb her. Unless there was a fire, or an intruder—Jehovah’s Witnesses didn’t count—we had all learned by swift-slap punishment that we were to respect her nap time. It was the one time slot of the day—thirty minutes or sometimes a whole hour—that our adult supervision was lenient. Occasionally, I would play bossy and order my siblings around on behalf of my mother, but for the most part, I left them alone to focus on my own debauchery and thus began my first real online relationship.

He was nineteen; I had turned twelve. My parents were seven years apart, so . . . I guess it was cool? He described himself as white, athletically built, bald, with a red beard. When I first saw American History X years later, in high school, I had a flash memory of him, as if I’d met him in a previous life. He was “pretty average looking” by his description, but by my imagination, he was beautiful. He was sensitive. He asked me—Jennifer was my white-girl name (same number of syllables as Jo-Issa)—about my day, about how I was doing. He expressed his feelings for me. Told me he felt stupid for thinking about me all the time when we’d never met. To him, I was blond-haired, blue-eyed, and petite. Technically, I was petite for an adult person, but definitely oversized for a sixth-grader.

Our conversations started out pretty casually at first, but they escalated quickly. And then he made the first move.

redbeard19: what are you wearing?

SuGaLuv112: a tank top and shorts

By then, I knew how to play the game. I had been asked the question via IM multiple times enough to know that a T-shirt, baggy jeans, and sneakers wasn’t sexy enough. With redbeard19, I was slightly seasoned, and he only helped me to get better. He taught me so much about what ideal sex was supposed to be, what I could expect from future relationships. This was the prelude to sexting. The crazy part is, nothing about this turned me on. It was a learning experience for me. I would type what guys wanted to hear, while reading Spider-Man comic books or as Tiny Toon Adventures played in the background, satisfied that, while most of my peers were still virgins, at age twelve, I was mastering the art of cybersex.

After that first time, I started to feel a sense of guilt. In the classroom, I was anxious, worried that eyes were on me. I started to wonder if what I did was wrong. What would my teachers think if they knew? My parents? Could people tell? Did I look different?

One day in the spring, I sat in Ms. Frank’s English class, unusually quiet. The teacher’s pet, I owned this class. She reminded the class of that often, which only escalated their hatred of me. But that day, sick and in pain, I just didn’t feel well. It was as if the butterflies inside my stomach had turned into dark moths, with razor-sharp antennas that were poking my sides and my midsection. I felt nauseous and dizzy. What was happening to me? I hadn’t even had real sex!

Ms. Frank excused me to the nurse’s office and I clutched my stomach and my throbbing head, worried about my pending diagnosis. I stopped at the restroom first to see if maybe I was experiencing a case of lunch food poisoning. And in that bathroom stall I discovered that, just like “Sally” in the Sex-Ed section of the Health textbook we had studied that winter, my body had begun to succumb to its transition to womanhood. Or as I thought at the time, Ew gross, my vag is bleeding.

I told the nurse I’d just gotten my period and she was super sympathetic, asking me if I wanted to go home. I did. I called my mother, who was transitioning into her new role as a stay-at-home mom and whispered my news into the phone.

“Mom, I got my pe . . .”

“What? Are you at school?”

“I don’t feel good.”

“What’s wrong with you?”

“I got my period.”

“Aww. My schubalubbalubba. I’m coming.”

During the car ride home, as my mom snuck peeks at me and patted my leg for comfort, I wondered if I were being punished for my “fast” behavior. In Health class, we learned that a girl’s period typically came around the time she was a teenager. I had just turned twelve. I was in a rush to grow up, but I didn’t know if I wanted to be “grown” yet. I didn’t want to be a woman, because that meant more responsibilities and expectations, and I was way too lazy for responsibilities and expectations. But then, my mom assuaged my worries with a simple declaration that changed everything for me.

“Guess you’re a teenager now.”

To hell with being a woman, I was a teenager. Teenagers like the kids on 90210 and Saved by the Bell. Finally! That was the missing link of my identity, and this bloody punctuation served as a head start to my new identity. I was a horny teenager.

My relationship with redbeard19 progressed as scanners became more readily available and he sent me a picture. He was nervous to do so, but he felt like I should see him. I was so excited. But also nervous. By then, I’d had several online flings here and there, but he was the only one with whom I had something “real.” Also up until then, his face was an open canvas. It could change depending on what he said, or my mood. He wasn’t a fully real person to me, with real feelings and real desires. He could have been lying to me in the same way that I was lying to him. We both could have had Tiny Toons on our television screens, scrambling to come up with novel sex words to stimulate each other. But the picture he sent demonstrated to me two things: 1) he was pretty damn ­honest—he appeared just as he said he would, and 2) he was actually kind of cute.

Something about our relationship wasn’t the same after that. I felt like a fraud, and I was kind of turned off by how vulnerable he’d made himself. I stopped becoming available to him at the same time every day. I’d block him whenever I felt like prowling for new people to talk to, then unblock him when I was bored. He grew hurt and needy, and I grew disgusted and cold.

redbeard19: what are you wearing today, baby?

SuGaLuv112: clothes.

redbeard19: take them off.

[5 minutes later]

redbeard19: u still there?

SuGaLuv112: sorry, was on the phone.

redbeard19: you don’t have time for me anymore

SuGaLuv112 has signed off.

After that, I kept him blocked. By now, I was becoming a pro. Some kids had after-school sports, some had piano lessons, but “cybering” was now my after-school activity of choice. And for the most part, it felt safe. I wasn’t “doing it” for real, so I was still pure. My actions were justified because I could still wear white for my future wedding (which, as with Zack and Kelly, would probably happen in college).

Now, pictures became a priority for me. If you didn’t have a picture, I wasn’t interested. As the most beautiful and sexy girl on the internet, I had a right to be picky. Not too much later, I met the guy of my dreams online. He sent me his picture after we got into a casual conversation about music. He was twenty-two, Italian, and black. He was one of the finest guys I had ever seen in my life, much less online. And he had multiple pictures of himself, so I knew it was real. Or was it? Thinking back, he sent me some very polished ­pictures—very modelesque. But whatever—he was real to me. I know he was real because he said he was Italian and black. And when we spoke on the phone, for the first time, he sounded like he was Italian and black; a Luigi-and-Tyrone hybrid, if you will.

His voice was so freaking sexy, though. I can’t recall what we would have talked about, what kind of engaging conversation ­starters came out of my twelve-year-old mouth. I just remember wondering why such a hottie like him was looking for people to talk to online. He seemed like the kind of guy who people would go out of their way to talk to. Just when I began to convince myself that this hot guy was courting me for me, he started pressing me for a picture. Shit. I had insisted that I didn’t have a scanner in the past, but in an effort to keep him around, so he wouldn’t get bored with me, I told him I planned to get one, just for him. So began the search. I’d have to do my best to find a picture that matched the description I gave him. He already thought I was eighteen. He thought I was African-American and light-skinned with long hair. So, thankfully, those nonspecifics gave me lots of options.

I don’t remember where or how I found the picture—but she was gorgeous. She was who I wished I looked like. She looked like she could have been mixed race. My middle school peers would be all over her. In fact, I’m pretty sure I printed her picture out and told all the guys she was my cousin. “That’s your cousin?! What side of the family? Where does she live?”

I sent him the picture, holding my breath. Would he believe me? Boy, did he! He was awestruck and excited, as if he’d hit the online jackpot. His interest in me grew: What did I do? Did I model? Was I dating? It felt amazing to be so beautiful. I envied the life of the real girl whose picture I stole. Did she know how lucky she had it? How easy her life was because she was so beautiful? And then the Blatalian wanted more. Maybe he was suspicious. Maybe he, too, felt like it was too good to be true. “Send me another picture,” he demanded one day.

My heart started racing. How was I going to find another picture to send him? Since I was now supposedly the proud owner of a scanner, I had no excuse. So I went on another online scavenger hunt, this time to try to find a girl who resembled the fake me. I found one; she was light-skinned with curly hair and posed in the shower, half-naked. She looked like she could have been partially Asian. But the initial picture I sent him was black-and-white and the new picture of the girl in the shower was in black-and-white, so I figured that he wouldn’t know the difference.

I was wrong. He confronted me on the phone. Partly amused, partly miffed.

“That’s not your real picture, is it.”

“Yes, it is.”

“You look like two completely different people.”

“People always tell me that when I curl my hair.”

“I don’t think either of these pictures are you.”

“Yes, they are.”

Not willing to argue with me about my fake identity, he pleasantly let me go. Ultimately, he stopped talking to me altogether. Lesson learned.

Eventually, the online conversations and fake adult sex no longer filled the void that my socially inactive middle school life had left wide open. My friends were being asked out. People were coupling up, and I was left with my lies and my fake personas. I needed someone to like me for me. Or at least who I pretended to be in person.

Table of Contents

Introduction xi

A/S/L 1

FAT 17

ABG Guide: Public Grazing 31

Leading Lady 35

ABG Guide: Connecting with Other Blacks 49

When You Can't Dance 59

Hair Hierarchy 69

ABG Guide: The Hair Advantage 79

Public Displays of Affection 83

African Dad 97

Dating Lessons & Summer Lust 117

ABG Guide: Black Women & Asian Men 137

Musical Ambitions & Failures 141

The Struggle 159

Halfrican 165

Fashion Deficient 179

New York, NY 187

ABG Guide: When Co-workers Attack 193

Acknowledgments 201

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?

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