‘Southside with You’: The real story behind the Obamas’ first date

Michelle was his adviser

In 1988, Barack Obama met Michelle Robinson after his first year of law school when he took a summer job at the upscale law firm Sidley & Austin in Chicago. For Barack, played by Parker Sawyers in the movie, it started as just a summer job to help him pay for his student loans. But the struggling law student quickly fell hard for Michelle, played by Tika Sumpter. Barack asked Michelle to go out with him over and over again, but she was his adviser and didn’t think it was appropriate. Until…

Hopeless romantic

Barack was so entranced by Michelle he offered to quit his job at the law firm. Sensing how sincere he was, she finally relented, much to Barack’s joy. “I remember being struck by how tall and beautiful [Michelle] was. She, I have since learned, was pleasantly surprised to see that my nose and ears weren’t quite as enormous as they looked in the photo I’d submitted for the firm directory,” he said in real life. 

A beater

In the film, Barack picks up Michelle in this rundown Nissan with a hole in the floorboard and an ashtray full of cigarette butts that is very similar to the one he drove in real life. It’s in this moment that Michelle learns that neither money nor fancy cars mean anything to Barack — instead, he’s solely focused on his mission to make the world a better place.

Two different worlds

Though Michelle Robinson didn’t grow up wealthy, she had a very different upbringing from Barack’s. She grew up in a stable, two-parent household, whereas Barack had a single mother who moved around quite a bit. “Michelle is from the South Side of Chicago and went to very white, Ivy League schools. Barack is of mixed race and had to consider race every second of every day — what it means to be pulled between two races and how to make peace with that. You can’t deny that when you are making a biography. You can’t deny who the people are, nor should you,” says Richard Tanne, the film’s director. 

‘The Sugar Shack’

In the film, Barack takes Michelle to an exhibit at the Art Institute of Chicago to see the paintings of Ernie Barnes, an African-American artist best known for his work called “The Sugar Shack” that was featured on Marvin Gaye’s album cover for I Want You. Barnes’ work was also featured on the TV show Good Times. It’s not known what art the real Michelle and Barack gazed at that day — most likely they were only looking at each other.

Community meeting

In real life, Barack didn’t take Michelle to a grass roots community meeting at a South Side church on their first date, but he certainly did later on in their courtship. The filmmakers thought that showing Barack give an inspiring speech in front of Michelle would be the perfect way to show her what Barack was capable of. It is the moment in the film when she sees him as more than just a cute dude. In her eyes, he becomes a man who can inspire America.

‘Do the Right Thing’

Just as in real life, Barack and Michelle go to see Spike Lee’s breakout film Do the Right Thing, about racial tensions in Brooklyn, New York. The film was nominated for two Academy Awards and four Golden Globes.

A divided America

It’s incredibly ironic that Do the Right Thing was the first flick the Obamas saw together, because it depicted America as a nation struggling to deal with racial and social tensions in both big and small ways. All these years later, these are the same issues Obama is dealing with as president, and Lee’s film likely provided an interesting perspective to young Barack. 

A love story

While politics and racial issues are certainly mentioned in the film, director Tanne didn’t set out to send a political message or to comment on race. Instead, he was inspired by what two people can accomplish together. “I wanted to tell a love story first and foremost,” he says in press materials provided by Roadside Attractions.

Unexpected run-in

In the film and in real life, Barack and Michelle run into a senior partner from their law firm at the movie Do the Right Thing. Their colleague is white and expresses a very different opinion of the film than Michelle and Barack seem to share, foreshadowing the racial divide the Obamas would later have to cross. But more embarrassing for Michelle, it’s clear to her co-worker that she’s on a date with her subordinate. Awkward!

Ice cream kind of girl

In real life and in the movie, Barack takes Michelle out for dessert. But it’s more than a scoop of chocolate ice cream the two end up sharing. “On our first date, I treated [Michelle] to the finest ice cream Baskin-Robbins had to offer, our dinner table doubling as the curb. I kissed her, and it tasted like chocolate,” he said. So sweet!

Michelle’s love for Barack

While it’s easy to see why Barack fell madly for the smart and beautiful Michelle, who seemed to have it all together, Michelle claims that Barack balances her personality in a way no other man could.

“If I had stayed in a law firm and made partner, my life would be completely different. I wouldn’t know the people I know, and I would be more risk-averse. Barack has helped me loosen up and feel comfortable with taking risks, not doing things the traditional way and sort of testing it out, because that is how he grew up. I’m more traditional; he’s the one in the couple that, I think, is the less traditional individual,” said the real Michelle. 

Director Richard Tanne

Director Richard Tanne says he always thought the bond Barack and Michelle share was special, but it wasn’t until he fell in love himself that he thought their story could be a movie. “I realized it wasn’t just kind of a meet-cute story about falling in love. It was also about finding that person who makes you a better version of yourself.”

Born and raised in Livingston, New Jersey, Tanne found early acclaim for his writing when he was just a teenager. He’s currently writing a feature film for Pixar.

What do the real Obamas think?

Director Tanne told Vanity Fair, “We’ve heard from some pretty reliable sources that they are aware [of the film]… They are excited. And they are also a little baffled by its existence.” It’s easy to understand why anyone would be baffled by a film about their first date with someone — particularly if the person making the film wasn’t on that date. But that’s what creative license is for.

Southside with You opens in theaters Friday. Rotten Tomatoes score: 91% RosieMeter score: 66%