In this chapter, the author describes her intimate relationship with Barack Obama. She states that as “soon as I allowed myself to feel anything for Barack, the feelings came rushing- a toppling blast of lust, gratitude, fulfillment, and wonder" (Obama 88). The author states that unlike other men she had dated in the past, Barack intrigued her the most. Barack seldom used his money for materialistic things but instead, his money went toward books (Obama 88). With time, Michelle was learning how Barack’s mind operated. In one instance, the author states that she woke up in the middle of the night, only to find Barack staring at the ceiling, obviously troubled. The author wondered if their new relationship was the cause of such worry, or perhaps his father’s death. However, when Michelle asked Barack what he was thinking about, he replied with a smile “I was just thinking about income inequality” (Obama 89). Barack’s answer made her realize how selfless her boyfriend was, and she wanted to know him on a deeper level.

Michelle recounts one of Barack’s community organizing meeting in Roseland. The author states that although the elderly women viewed Barack with skepticism, Michelle realized that her boyfriend was not the kind of person to be bothered by cynicism, but instead was a man “used to having to prove himself” anywhere he went (Obama 91). His odd heritage, unusual name, and love for books made Barack a unicorn. Unlike Michelle who strived to get herself out of Chicago, the author asserts that Barack was a visionary who tried to get the “place itself unstuck” (Obama 92).

Michelle’s father’s health deteriorated making him trade his “car for a specialized van to accommodate his disability” (Obama 93). At the same time, Barack was moving back to Harvard Law School leaving Michelle behind, after only knowing each other a couple of months. To manage their long-distance relationship, both Michelle and Barack agreed to keep communicating through phone calls. The rest of the chapter details Michelle's job at Sidley & Austin working as an African American woman on the hiring team. The author also chronicles her visit to Honolulu, Barack's home. During this visit, Michelle realized that although they both came from different backgrounds, they both fit together in an intriguing way (Obama 96). The chapter closes with Michelle writing about the death of her close friend Suzanne who succumbed to illness at the young age of twenty-six.