Was Barack Obama terrible to date? An investigation 🔎
Barack Obama’s memoir, A Promised Land, is, at last, out in the world and it’s a 700-page exercise in painstaking legacy-burnishing. Obama, with his characteristic deliberateness, relitigates every decision he ever made in the White House, but if he wanted to focus my attention on how evil Senate Republicans actually were or if it was really necessary to deport all those people (it wasn’t), he should have not BEGUN in the first chapter with this riveting yet completely unnecessary revelation:

This paragraph, it’s art. The labored euphemism of “women I was attempting to get to know.” The descriptions of these sweet Occidental co-eds as “long-legged” “smooth-skinned” and “ethereal” (???), that would make Danielle Steel blush. The very thought of Obama, future leader of the free world, poring over Marx and Fanon, so he could drop a casual but incisive observation betwixt the stacks.
Which brings us to the question that has been plaguing me for more than a decade, ever since Barack Hussein Obama burst onto the national stage. What was it like to date our unquestionably hottest and coolest living president (with apologies to Jimmy Carter)? Was it possibly... a little bit terrible? Blessedly, we have a voluminous body of work to consult.
Look, do I think it’s good that my brain is so addled, that my worldview is so inflected by Nora Eprhon and also the patriarchy, that American political culture encourages us to view monstrously powerful people as celebrities that I evaluate many of them on the basis of “Is this person bonable/boyfriend material?” No, I think it’s probably pretty bad, but it is just where I’m at.
Young Barack appears to have had three prior serious girlfriends before Michelle (B.M.), as outlined in “Barack Obama: The Story” by David Maraniss (big excerpt in Vanity Fair) and “Rising Star: The Making of Barack Obama” by David Garrow.
First, there was Alex McNear, an Occidental student who edited the literary magazine where Barack once submitted poetry and who he reconnected with in New York after transferring to Columbia. Alex and Barry took long meandering walks through Manhattan over the summer of 1982, and after that, when she moved back to California, exchanged long, meandering letters. Their main mode seemed to be to try to outdo each other with their literary prowess. We are going to give them a break because they were 20 years old, and if I’m being honest, I swoon for a man who would read a whole-ass book to get with me, but it’s hard to give Barack his props when his love letters are like this:
Remember how I said there’s a certain kind of conservatism which I respect more than bourgeois liberalism—Eliot is of this type. Of course, the dichotomy he maintains is reactionary, but it’s due to a deep fatalism, not ignorance. (Counter him with Yeats or Pound, who, arising from the same milieu, opted to support Hitler and Mussolini.)
A milieu?? Of Yeats, Pond and Eliot? Guess who said it: Timothée Chalamet’s character in Lady Bird or a young Barack Obama.

Barack also had writerly aspirations, and YOU COULD TELL. In the same letter:
Moments trip gently along over here. Snow caps the bushes in unexpected ways, birds shoot and spin like balls of sound. My feet hum over the dry walks. A storm smoothes the sky, impounding the city lights, returning to us a dull yellow glow.
There are just so many verbs. Perhaps you knew this try-hard person in your college creative writing class and maybe, you were dumb enough to find that person a little bit sexy. Perhaps you WERE this try-hard person in your college creative writing class and no one found you sexy, an injustice.
Barack broke it off with Alex in the same manner as he carried on the romance: verbosely. “When I see you, the palpitations of the heart don’t boil to the surface,” he wrote. “When I sit down to write I no longer feel the need to bleed for brilliance on the page.” Ouch.
The romance: 😍😍😍😍
The terribleness: 👎🏽👎🏽
It didn’t take long for Barack to rebound. A few months later, at a Christmas party in the East Village, he struck up a conversation with Genevieve Cook, an Australian grad student. “I’m pretty sure we had dinner maybe the Wednesday after. I think maybe he cooked me dinner,” Genevieve later told Maraniss. “Then we went and talked in his bedroom. And then I spent the night. It all felt very inevitable.” The moves!

Genevieve was an avid diarist who documented their relationship in intimate detail. That’s how we know that Barack liked to lounge around on Sunday mornings in a blue-and-white sarong and do the NYT crossword. It’s how we know he was an “earthy” lover, as Cook described it. (What does this mean? I don’t think I’m ready to know what this means.)
One time, Genevieve challenged Barack to a friendly sprint in Prospect Park. She beat him, he did not take it well:
Barack couldn’t really believe it and continued to feel a bit unsettled by it all weekend, I think. He was more startled to discover that I had expected to win than anything else. Anyway, later in the shower (before leaving to see The Bostonians) I told him I didn’t feel that good about winning, and he promptly replied probably cos of feelings of guilt about beating a man. In which case, no doubt, he’d already discovered the obverse feelings about being beaten by a woman.
A bad look. He was this also this guy, again per Maraniss’s biography:
When she told him that she loved him, his response was not “I love you, too” but “thank you.”
This dynamic portended trouble ahead for the young couple: Genevieve became increasingly frustrated at how Barack kept himself at a cool remove. They moved in together, briefly, while he was in between jobs and apartments, but their relationship had deteriorated so much during this period that she told a friend, “I just wanted to chop his d–k off.” I don’t know what he did to prompt this reaction and but I am firmly team Genevieve.
The romance: 😍😍😍
Terribleness: 👎🏽👎🏽👎🏽
Finally, there was Sheila Miyoshi Jager, an anthropologist who he fell in love with while working as a community organizer in Chicago and nearly married. Sheila and Obama had what sounds like a lovely relationship and then one that was messy as hell, as Obama tried to square his race, identity and political aspirations with being with another biracial woman (Sheila was half-Japanese and half-Dutch). I do not have the wherewithal to pass judgement on a situation this thorny but I do want to tell you that he waffled forever about marriage culminating in a protracted fight at their friend’s weekend house that went like this, according to Garrow:
From morning onward “they went back and forth, having sex, screaming yelling, having sex, screaming yelling.” It continued all day. “That whole afternoon they went back and forth between having sex and fighting.” Others remember “moving around to the other side of the porch just to be able to talk.” It “was a long weekend” and “an incredibly unpleasant one,” one person recalled. “It was so stressed and tense.”
This is just bad manners!!!!
Romance: 😍😍
Terribleness: 👎🏽👎🏽👎🏽
We know the rest: Sheila and Barack broke up, he went off to Harvard Law School and took a summer internship at Sidley Austin in Chicago, where he was assigned one Michelle LeVaughn Robinson as a mentor. On their first date, they went to the Art Institute, took a walk, and saw Do the Right Thing. “Take tips, gentlemen,” the president has said, ever so humbly.
Barack has transformed into a full Wife Guy now—his pithy Instagram captions about how Michelle is the smartest, the prettiest, the best are better than all those old love letters. A weary nation rejoices.
Was it ultimately terrible to date Barack Obama? I think I’d say if you can at all swing it, best to avoid dating future presidents.