In 1989 Chicago, a young lawyer, Michelle Robinson, reluctantly agrees to spend the day with a promising law associate named Barack Obama. Michelle, who is cautious about any romantic advances from Barack due to their professional relationship, maintains that this is not a date. Their day begins with a visit to an Afrocentric art exhibit at a local cultural center, where they engage in deep discussions about identity, community, and their personal aspirations. Despite Michelle's initial reservations, Barack’s charm, intellect, and earnestness begin to make an impression on her.

As the day unfolds, they attend a community meeting where Barack delivers a compelling speech that further demonstrates his passion for social justice and community organizing. Throughout their time together, they share heartfelt conversations, revealing more personal facets of their lives and backgrounds. The day culminates in a memorable moment that subtly shifts Michelle’s perspective on Barack. By the end of their time together, both Michelle and Barack gain a newfound appreciation for each other's values and vision for the future, setting the foundation for what would become a significant relationship.