The main challenge Southside With You sets for itself isn’t a very difficult one. Richard Tanne’s gentle romantic drama charts a first date from its uneasy opening to its hopeful conclusion, with its protagonist Michelle Robinson (Tika Sumpter), as a skeptical young lawyer being wooed by subordinate at her firm. The film, at times, tries to cheekily inject some suspense into whether she’ll be won over. But given that her associate is a young Barack Obama (Parker Sawyers)—her future husband and President of the United States—the film inspires very little “will they, won’t they?” nail-biting.
So the real task for Southside With You may be justifying its own existence. In portraying Michelle’s cautiousness and Barack’s halting, but eventually successful charm offensive, the first-time writer-director Tanne revels in the qualities Obama would later use to captivate much of the country. But with President Obama still in office, there’s a sense that it may be too early to retell the story of his and Michelle’s first date—even if the election for his successor is still months away. But leave the oddity of Southside With You’s existence aside, and the film is still compelling for the way it celebrates a powerful partnership by unraveling its earliest moments.
Barack’s side of the first date is more widely known, since he recounted it in his memoir The Audacity of Hope. But the basics are: The pair met at the law firm where she worked and where he was a summer associate. They went to see Spike Lee’s Do the Right Thing, which had just been released in theaters, and shared an ice cream cone afterward. But in Southside With You, Tanne wisely positions Michelle as the audience surrogate, slowly getting to know Barack as he tries to convince her he’s worth her time.
With the question of a happy ending out of the way, Tanne’s script invests itself more in Michelle’s psychology—including her tightly wound sense of propriety, rooted in her efforts to fit in at institutions (Princeton, high-powered law firms) where she’s one of few black women in attendance. Worried about how their relationship might look to others, Sumpter plays Michelle with her guard up, often deflecting Barack’s attempts to flirt with terse dialogue. Sumpter’s performance may be a little stilted at times, though it speaks to the character she’s playing. Michelle is saddled with heroic amounts of exposition, laying out her life story, and her hopes and fears, while learning more about Barack’s past. But Sumpter sells Michelle’s deeper emotions beautifully through her loving lionization of her family and upbringing, and her simmering resentment over her tenuous status at the firm.
If Southside With You is a love story, its job is to get audiences to fall for Obama: Tanne films his subject with all the subtlety of a campaign ad, bathing him in heavenly light or putting him in dramatic silhouette. Sawyers is not exactly a dead ringer for the president, but he’s close enough, and Tanne does the rest with his camera to make the physical resemblance nigh-uncanny. As a result, there’s a spookiness to Sawyers’ performance, which carefully treads the line between acting and mimicry.
The young Obama’s voice and diction are particularly dead-on when he’s in a political mode, especially in what comes closest to the film’s set piece: Barack talking at a community meeting at a local church in the South Side of Chicago. That meeting was the ostensible reason for his and Michelle’s date, a non-romantic excuse for them to intermingle outside of the office (he springs the Spike Lee movie, and the ice cream, on her later). It’s also the moment for Tanne to have the most fun with the odd premise of his film, forsehadowing Obama’s effortless ability to connect with a crowd, even though this time it’s just a dozen people sitting in church pews.
Fortunately, whenever Southside With You threatens to get too cute, it pulls back a little. When Michelle asks Barack if he’s thought about a career in politics, he replies “maybe,” with a shrug, taking another drag on his cigarette. For the most part, Tanne resists having his characters wink to the camera, relying instead on the power of Sawyers’ and Sumpter’s performances. In a tumultuous election year, Southside With You is a gentle, rose-tinted piece of political nostalgia—one that glances at the divisions in American society, but still casts a optimistic view toward whatever’s next.