Embracing the Awkward, One Webisode at a Time

With her Misadventures of Awkward Black Girl Web series, Issa Rae captures the angst of brown women everywhere -- and has caught Hollywood's attention in the process.

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?' "