Darius and Nina meet at a poetry reading in Chicago and immediately feel a strong attraction towards each other. Over the course of several weeks, they go on dates, talk about their careers and past relationships, and attend various artistic events around the city. Their friends, including Darius' best friend Savon and Nina's close confidante Josie, offer their own perspectives on love and relationships.
Nina is hesitant to commit to a serious relationship with Darius due to a previous failed engagement, but Darius is persistent in his pursuit of her. They eventually sleep together, and their physical connection deepens their emotional bond. However, when Darius reveals that he has a job offer in New York City, he must decide between pursuing his career dreams or staying in Chicago to be with Nina.
At the same time, Nina's ex-fiancé Marvin comes back into the picture, causing tension between her and Darius. Nina and Darius eventually have a conversation about their future together, and Darius decides to stay in Chicago with Nina. However, as they try to navigate their relationship, misunderstandings and miscommunications cause rifts between them.
In the end, Darius and Nina realize that they truly love each other and make amends. The movie ends with Darius reciting a poignant poem about their love, leaving viewers with the sense that their relationship has a chance at lasting forever.