The chapter starts with Michelle waiting for Barrack Obama to arrive at her office to begin a mentorship program. A senior partner had requested Michelle to mentor an incoming summer associate, to which she willingly agreed.  Like Michelle, Barrack was an African American, born and raised in Honolulu, “the son of a black Kenyan father and a white mother from Kansas” (Obama 80). Over a couple of weeks, Michelle and Obama had become acquainted with one another and had established a routine where the two of them had lunch whenever they had time.

The author informs the readers that parts of the South Side had “become desolate as business shut down and families continued to move” (Obama 79). The increasing use of drugs in Chicago lead to rival gangs fighting for the market share, hiring young boys to sell drugs on the streets instead of going to school. Obama writes that she hated any kind of drugs including smoking, and apparently, Barack lighting a cigarette after they had had lunch snuffed out any interest, she might have in him (Obama 81). With time, Michelle realized that she and Barack shared a lot and their workplace association ultimately turned into romance.