Southside with You 2016

It is the summer of 1989 in Chicago, Illinois, when Barack Obama and Michelle Robinson are preparing for what she insists is not a date. Despite his persistent invitations since the start of his summer internship at the law firm where she works as a second-year associate and his advisor, Michelle is adamant that their outing is purely professional. As she gets ready, she pays meticulous attention to her appearance, living with her family who teasingly question her about looking nice for what she asserts is just a community meeting. Michelle reminds them they taught her the importance of looking her best, maintaining her stance that this is no date.

Barack’s approach is far more casual. He relaxes at his cluttered apartment, chatting with his grandmother about his plans, who advises him not to be late. He throws on a shirt and heads out in his aging Datsun Sentra, nervously smoking a cigarette until he arrives at Michelle’s house. Once outside, she chides him for being late, and he sheepishly admits she’s right, causing her to remind him of his tardiness on the first day of his internship. Despite her insistence on sticking to their plan for the community meeting, Barack suggests a detour to the museum, claiming they have hours to spare. Though initially annoyed, she relents, agreeing to visit the museum before their meeting.

During their drive, they discuss work, specifically a recent court motion that Michelle predicted would fail. She shares her frustration about not being heeded by the firm’s partners, feeling they wasted time and resources, to which Barack inquires about her real frustrations. At the museum, Barack impresses Michelle with his knowledge of art, particularly the works of Ernie Barnes, revealing an understanding of its cultural significance.

They share lunch in a park where Michelle insists on paying since this is not a date. Their conversation flows from favorite foods to personal histories. Barack opens up about his mixed heritage and strained relationship with his father, while Michelle reflects on her family’s struggles and how they shaped her values. As they travel toward the community meeting, she confronts him about his privileged position at Harvard and the law firm, suggesting they both share the same sell-out mentality. The tension serves to deepen their connection, unveiling layers of understanding between them.

At the meeting, the community members express their anguish over failing to secure funding for a center. Sensitive to the group’s sentiments, Barack steps up to address them. His speech balances urgency and hope, emphasizing the need to persevere despite setbacks. His natural charisma captivates the crowd, and Michelle can’t help but admire his ability to inspire.

Afterward, Michelle confronts Barack about possibly manipulating the situation in his favor, yet she seems to forgive him as they share dinner and discuss their past experiences. They bond over shared frustrations about their lives, and after watching Spike Lee’s Do the Right Thing, an emotionally charged moment prompts Michelle to hold Barack’s hand.

Their evening closes with an awkward encounter as Michelle runs into a partner from her firm, desperate to maintain the façade that their outing isn’t a date. Barack deftly navigates the conversation, impressing the partner with his insights. But during the car ride home, Michelle expresses her discontent over the evening and the potential gossip it could stir at work. In an unexpected gesture, Barack stops for ice cream—chocolate, her favorite. As they sit together in silence, a sweet moment unfolds when she offers him a taste, leading to a tender kiss that signifies a turning point in their relationship. After this shared intimacy, he takes her home, leaving both of them to reflect on the complexities of their connection.