Embracing the Awkward, One Webisode at a Time

Issa Rae Presentations

Remember the first day of school? Sweating through your gym uniform waiting to get picked for kick ball? Walking into a bustling lunchroom with a tray full of Tater Tots and a heart filled with hope? Back then you knew the meaning of "awkward" before you even knew how to spell it.

Too bad you didn't also know Issa Rae. Rae — writer, director and star of the popular Web series The Misadventures of Awkward Black Girl — has made it her hilarious mission to capture the angst of awkward girls (black or otherwise) everywhere — those awwwwkward moments that carried over from middle school to the mid-20s.


"I wanted to tell this story and I thought, 'If I don't start it myself, I'll never get it done,' " Rae, 26, told The Root. "We're not all ugly. We're not all desperate. We're just normal, awkward girls trying to find ourselves."

Rae plays J, the passive-aggressive diet-pill pusher who hates confrontation, despite thinking that all her co-workers "are pretty much the worst people in life." She writes violent rap lyrics as a coping mechanism and is truly, madly, secretly in love with her co-worker Fred.

And instead of telling everyone how she really feels, J deflects by obsessing over life's little things, like the proper protocol for when you repeatedly run into someone in the hallway. Do you pretend you don't see them? Stare at the totally blank walls?

"[The show] is an extension of me," she said. "I'm definitely not that bad. That was me maybe in middle school. J's way more insecure and socially conscious than I am.


"There are no quirky black comedies out there," added Rae, who lists Curb Your Enthusiasm, Seinfeld and Arrested Development as her must-see TV. "Where is that in the black community?"

But the show is not just for the black community — Rae's razor-sharp one-liners cut across color lines. "Hair is the best thing to happen to rhythm-less nonblacks," jokes J, who admits in last month's episode that she can't dance. Sure, the joke is ostensibly about race. But who hasn't seen someone "whipping their hair" because they couldn't "do the wop"?


"Issa is telling universal stories with characters we're not used to seeing," said Andrew James, who plays A, the office nerd with whom J had a regrettable one-night stand. "I believe black people and nonblack people are yearning for these characters without even realizing it."

Nearly every day, Rae gets "hit up" by other awkward black girls who wonder how the screenwriter knows so much about their constant struggles with self-consciousness. " 'I swear you're hiding in the bushes and filming my life,' " Rae quoted from her growing fan mail. " 'This is my story! How did you know?' "


Rae sent a similar letter to Love & Basketball director Gina Prince-Bythewood nearly a decade ago. "That movie just changed me," she said. "It was a simple love story. I hadn't seen that. And the fact that it was written, produced and directed by a black woman made me think that I could do it, too."

So a 16-year-old Rae did just that. She wrote her own feature film and promptly sent it to Prince-Bythewood for feedback.


The acclaimed writer-director actually wrote Rae in return, encouraging the budding screenwriter to keep at it.

"The fact that she wrote me back was just the tightest thing in the world to me," said Rae, a Los Angeles native who went to Stanford University to major in African-American studies and political science.


While at Stanford, Rae met Tracy Oliver, who plays Nina, the mean girl, on the show. The two became friends and writing partners. Their goal back then, according to Oliver, was to become "the black female Matt Damon and Ben Affleck.

"We've always worked really well as writing partners because we're both incredibly silly and immature, which is horrible for making great life decisions, but amazing for writing comedy," Oliver said. She explained that it's Rae's star power that draws viewers to the show. "She is a beautiful, dark-skinned, intelligent woman with natural hair in a leading role. That's huge."


Rae figured that ABG would be popular among her friends and it would be a great way to showcase her talents as a writer, producer, director and actress. But the series quickly went "mildly viral," as Rae calls it. Each episode averages more than 40,000 viewers, not bad for a show whose episodes she thinks up in the shower.

"I'm writing this pretty much off the top of my head," said Rae, who is now represented by United Talent Agency and 3 Arts Entertainment, which also represents comic writers Tina Fey, Amy Poehler and Donald Glover. "It's just crazy to me."


Rae said she is "just writing, writing and writing." Her team is working to develop ABG as a cable series, but in the meantime, Rae is focused on J's story.

"I hope she finds herself, and I really hope she becomes comfortable with herself," she said, "but I don't see that happening anytime soon."


Look for the newest episode of The Misadventures of Awkward Black Girl July 7.

Helena Andrews is a regular contributor to The Root and author of Bitch Is the New Black, a memoir in essays. Follow her on Twitter.


Helena Andrews is a contributing editor at The Root and author of Bitch Is the New Black, a memoir in essays. Follow her on Twitter.

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