In the summer of 1989, future history books will teach the children of the world, 25-year-old Chicago lawyer Michelle Robinson reluctantly went on a non-date-date with a cute Harvard Law student named Barack Obama that changed America. That day is the subject of writer-director Richard Tanne’s romantic drama Southside with You, in which White House lore becomes Tinseltown legend as the first couple’s first date unfolds over the course of one epic walk ’n’ talk, a la Before Sunrise. It is impossibly adorable and, frankly, will be irresistible catnip to fans of the exiting Obamas. But how legit is this piece of presidential bio-fiction?
Premiering the indie in January at Sundance to an audience of overwhelmingly charmed critics (guilty as charged—read my review here), director Tanne admitted that “the trajectory of the date,” pieced together from public record and interviews, is “about 90 percent accurate.” Warm performances by star-producer Tika Sumpter and newcomer Parker Sawyers carry the film, which is highlighted by Sawyers’s spitting likeness to the real Obama and his ability to nail the 44th POTUS’s effortlessly charismatic swag.
Like many a legendary first date, the Obamas’ still very meme-worthy romance began as something… not quite official. Michelle, a hard-working and ambitious black female lawyer in a company and field dominated by white men, had graduated cum laude from Princeton and parlayed her Harvard JD into a gig at Chicago’s Sidley Austin law firm. According to a Washington Post profile, she’d told her mother that summer that she was going to focus on her career and not worry too much about dating.
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Michelle was assigned to mentor the 27-year-old Obama during his stint as the firm’s summer associate—and by many accounts was determined not to date him. To Obama: From Promise to Power author David Mendell, Michelle explained her apprehension at the young chain-smoking biracial charmer from Hawaii. “I had dated a lot of brothers who had this kind of reputation coming in, so I figured he was one of these smooth brothers who could talk straight and impress people,” she said.
Of course, as Southside with You opens, both Michelle and Barack are bristling with excitement as they get ready for their first solo hang—she, primping at home while denying it’s a date, and he, coolly smoking a cig while reading a book in a wife beater. Did a young, sexy, book-loving Barack really blast Janet Jackson’s No. 1 hit “Miss You Much” while driving across town to swoop Michelle in his beat-up yellow Datsun?
Was he also, as Southside with You suggests, instantly flirty, looking Michelle up and down like a starving man seeing food for the first time in his life? I’d like to think so (although only President Obama knows the real truth). David Maraniss’s Barack Obama: The Making of the Man confirms at least that yes, Obama drove a terribly beat-up yellow Datsun, one that did indeed have a hole in its floorboard, He’d bought the car for $500 after returning to the States from his soul-searching stint in Europe and Africa.
The ostensible purpose of Michelle and Barack’s “date” was to attend a community meeting on the South Side as colleagues. But first, the movie says, he hustled her into a pre-meeting stop at the Art Institute of Chicago to take in an art exhibit. In the film an angry Michelle relents, then is impressed when the young, smooth-talking Obama drops serious knowledge about the work of African-American actor and painter Ernie Barnes and his iconic “Sugar Shack.”
We may not know what artwork the Obamas bonded over that day. But both the president and the first lady agree that taking that gallery detour was a pretty smooth move. “It was a cool date, actually,” Michelle admitted years later in a White House promo video the couple posted to Obama’s YouTube page. “We spent the whole day together. He was showing me all facets of his character. He showed his cultural side, and then we took a nice long walk down Michigan Avenue.”
In the video, her husband smirks at the memory and addresses the men out there watching: “Art, guys out there—it impresses people.”
The Obamas had their historic first meal together by the fountain in the Art Institute’s courtyard, although the film shows them eating sandwiches in a park. There, in the film, they get to know each other a little better: She hates pie, but loves ice cream. He hates ice cream, and maybe also his dead father. They share their frustrations, ambitions, hopes, and dreams, and start testing each other, pushing each other’s buttons, and glimpsing the untapped potential the other can’t quite see.
Michelle, years later, told author Mendell that the lunch didn’t quite convince her she was wrong about Barack. “So we had lunch, and he had this bad sport jacket and a cigarette dangling from his mouth, and I thought: ‘Oh, here you go. Here’s this good-looking, smooth-talking guy. I’ve been down this road before.’”
But then they walked, and talked, and made it to the community meeting in a church where Obama spent his pre-Harvard years working for the Altgeld Gardens public housing development. It’s a crucial moment for Movie Michelle, who watches as the playful Obama transforms in front of her eyes into a stirring public leader, rallying frustrated citizens into persevering for the future. After that, their crackling chemistry and tentative attraction builds over beers that may or may not have happened—even as she maintains her distance, worried that the hard work she’s had to put in at work just to be taken seriously will be erased if she begins dating her junior associate.
In a highly effective move, the will they/won’t they drama of Southside with You climaxes with an incident that very much did happen in real life—kinda. Hitting the movies to check out Spike Lee’s controversial new joint Do The Right Thing, the pair find themselves face to face with Michelle’s nightmare: a senior white partner from their law firm, who’s also come to check out the movie. Like Southside’s brief mention of Obama’s white girlfriend at Columbia, the name of the real partner is changed onscreen. “Avery” and his wife Laura were really lawyer Newton Minow and his wife Jo, who ran into the future Mr. and Mrs. Obama at the movies. “I think they were a little embarrassed,” Minow told The Washington Post.
Unfortunately, the film uses him for its own dramatic purposes: to play up the racial and cultural frictions that theoretically gave Barack and Michelle common ground as two of the only African-Americans at the office, and to justify Movie Michelle’s fears that the older white men of Sidley Austin might lose respect for her as an attorney in her own right if she started dating Barack.
Those racially-charged frustrations, portrayed purposefully onscreen by Sumpter, have not been expressed much by the real Michelle and Barack in interviews about their romance. Remembering their first date in that 2012 YouTube video, they’re all smiles. “He showed all the sides,” said Michelle, giving props to the grinning president. “He was hip, cutting-edge, cultural, sensitive—the fountain, nice touch. The walk—patient.” President Obama grins, glances again into the camera. “Take tips, gentlemen.”
What is indisputable in Southside with You is how that legendary date ended, three years before they’d eventually be married: with a first kiss over ice cream outside the Baskin-Robbins in Chicago at the intersection of Dorchester and East 53rd Street, where a plaque now commemorates the historic moment.
“On our first date, I treated her to the finest ice cream Baskin-Robbins had to offer, our dinner table doubling as the curb,” the plaque quotes President Obama as saying in an excerpt from a 2007 interview with Oprah’s O Magazine. “I kissed her, and it tasted like chocolate.”
