The Obama Girls' First Day of School

As the first daughters begin classes at Sidwell Friends, the author reflects on his time as one of its few black students.

01.05.09 6:06 AM ET

Dear President-elect and Mrs. Obama,

You’ve been there. Princeton. Columbia. Harvard Law. The white-shoe law firm of Sidley Austin. The US Senate. You know what it’s like to be that raisin in the milk, the rare black face at an elite institution.

As your daughters come of age at the top prep school in our nation’s capital, they will likely face the same raisin-in-the-milk trials and awkwardness with which you are likely familiar and I most certainly am; I attended the same school, Sidwell Friends, for six years, graduating in 1995.

There are some important differences between my Sidwell experience and what your daughters will face, of course.

As your daughters come of age at the top prep school in our nation’s capital, they will likely face the same raisin-in-the-milk trials and awkwardness with which you are likely familiar.

I enrolled at Sidwell to avoid a public school where students regularly got stabbed. D.C. was overrun by crack dealers, photos of whom my mother liked to take from our living room window. Malia and Sasha, on the other hand, are transitioning from the Gothic halls of the University of Chicago Lab School.

My Sidwell fees were covered by scholarships, my part-time job, and the incredible sacrifices made by my mother. For you, paying Sidwell’s $30,000 tuition will likely require less creative financing.

The face of my household was a single black woman who never finished college. Your faces, on the other hand, are commemorated on memorabilia for sale during nearly every commercial break on cable television—and possibly on a new currency someday, if you play your cards right.

One thing you won’t have to worry about: Sidwell will assuredly meet the challenges of educating and providing security for the first daughters. Back in my day, Sidwell parents included three senators, the publishers of both The New York Times and Washington Post and, oh yeah, Bill and Hillary Clinton, whose pubescent progeny was two years behind me. The Roosevelts, Nixons, and Gores also sent their kids to Sidwell.

But what may prove more challenging is the burden Malia and Sasha will face, not as first daughters, but as plain ol’ black girls. They already represent the United States of America, but in a school like Sidwell, even though it may have a greater representation of minorities than in my time, they also will be expected to represent the United States of Black America, as I was.

They’ll be The Black Friend. They’ll suffer through many a white person wanting to touch their hair. (I strongly recommend Sasha and Malia avoid cornrows.) And they will likely be viewed as both exceptions to and spokespeople for their race. This means they should be prepared when fellow students and even teachers turn to them for “expertise” when the curriculum touches on anything black.

Black Sidwell students are often likely to end up being the only black kid in a classroom. When this happens, we are automatically deputized as a sort of Assistant Professor X. During a discussion of Uncle Tom’s Cabin, Hurricane Katrina, or even Black Lung, all eyes swivel toward us as everyone expects us to break out our copy of The Negropedia: A Comprehensive Guide to All Black Knowledge for the Edification of White Folks. Let your daughters know this moment is coming. Drill them on black facts. Make them memorize Roots. This way, they can prepare their lesson plans in advance.

It’s not just the interaction with white people that may test your daughters and vicariously cause you flashbacks. The already small black population at a school like Sidwell can find ways to further divide itself over petty nonissues of black authenticity. Let’s just say you may have to reacquaint yourself with the term “Oreo.”

I joined Sidwell in seventh grade. My first day at school, a black student who’d attended since kindergarten pulled me aside and asked if I knew what an Oreo was. “Yeah,” I answered. “It’s a cream-filled chocolate wafer manufactured by the Nabisco Corporation since 1952, and it’s mad tasty.” He corrected me: “No, an Oreo is somebody who’s black on the outside and white on the inside.” He then pointed across the room. “See Darryl? He’s an Oreo.”

What I saw was a slightly nerdy black kid hanging out with some white friends. What I failed to see was the problem. Being nerdy was practically a prerequisite for admission, and with the small number of black kids at Sidwell, it’d be a pretty lonely life for a kid with no white friends. Besides, isn’t the point of being black at an elite prep school to collect as many white friends as possible for later use?

Given your backgrounds, you are likely better equipped than my mother was to help usher your daughters through these racial high-wire rites of passage, but be prepared for Georgetown parents to differ from the parents you knew on the South Side of Chicago in the bosom of the U of C. I recall my mother returning from school meetings frustrated by white parents whose subconscious racist assumptions were invisible to them because they called themselves liberals (e.g. “If you’re gonna have a black student union, why not a white student union?”).

Be prepared to hear “I’m not racist. I voted for you!” as an excuse for such closed-mindedness, ignorance, or worse. Mark my words, this will be our era’s equivalent of “I’m not racist. I have a black friend.”

One final lesson: Sidwell Friends draws proudly on its roots in the Quaker religious tradition of nonviolence, consensus decision-making, and social justice. (Don’t be surprised if your little girls come home challenging Daddy’s foreign policy.) Contrary to my initial thoughts, however, these Quakers, who were the first American institution to ban slave-holding, have absolutely nothing to do with Quaker Oats; no oatmeal discounts, no profit-sharing. Nothing. Please make sure this distinction is clear to your daughters, who will have a tough enough time maintaining their new positions as spokespeople for Black America.

Baratunde Thurston is a conscious comic and a vigilante pundit who works as an editor for The Onion. He was nominated for the Bill Hicks Award for Thought Provoking Comedy, declared a Champion of the First Amendment by Iowa State, and called “someone I need to know” by Barack Obama. He co-founded and writes under the name Jack Turner for Jack & Jill Politics, billed as “a black bourgeoisie perspective on U.S. politics” and one of the top 10 most popular black blogs in the country. He has written for The Huffington Post and the UK Independent and comments frequently on NPR, the BBC, and CNN. He performs stand-up regularly in New York City. He is a graduate of The Sidwell Friends School and of Harvard, where he wrote for The Crimson.