It is the summer of 1989 in Chicago, Illinois. Barack Obama and Michelle Robinson are getting ready for not a date. She's been very clear that this is not a date, despite him asking her to go on a date almost since the beginning of his summer internship at the corporate law firm where she is a second-year associate, and his advisor. She maintains that it would be inappropriate and a distraction if the two of them went out on a date, so although they are planning to spend time together, it is definitely not a date. Michelle prepares carefully, working to look her best. She lives with her family, and her mother and father tease her about making herself look pretty for not a date. She replies curtly but lovingly that they taught her to always look her best, and maintains that its not a date its a community meeting that sounded interesting, so they are going to it together, but that's it. Barack prepares almost not at all.
He is smoking in his cluttered apartment, talking to his grandmother on the phone about the woman hes going to see. She tells him he needs to get going in order not to be late, and he tells her it will be fine, but eventually he hangs up, throws on a dress shirt (no tie) and heads out to his car, a beat-up Datsun Sentra. He smokes nervously in the car until he pulls up near Michelle's house, takes two quick puffs on a cigarette, puts it out, sprays breath spray into his mouth, and then around the car, and heads out to pick her up. He finds Michelle outside her house; he never meets her family.
She says that hes late. He says that he was hoping she wouldn't notice. She says that he was late for his first day as an intern at the law firm. He comments sheepishly that she noticed that too. She points out that as his advisor, its her job to notice. She says that they should get to the community meeting, but he says that they have time several hours, in fact, and he was hoping they could go to the museum to see an art exhibit first. Shes mildly upset at this, but he assures her that if she says its not a date, then its not a date until she says it is, and she agrees to go.
When she gets in the car, she notices the cigarettes in the ash tray, and a hole in the floorboard. She can see the street beneath her feet. On the way to the museum, they discuss a case at work, where a motion in court has failed. Barack asks if Michelle is upset that the motion failed, and she replies that shes glad it failed. Shes frustrated because she said six months earlier that the motion would fail, and in her mind, the firm wasted six months of effort making the motion because a senior partner didn't listen to her advice to not file the motion in the first place.
Barack asks if its really the law firms partners shes frustrated with. At the museum, Barack points out the art of Ernie Barnes. Michelle expresses surprise that he would know anything about art. He responds by describing the history and technique of Ernie Barness art at length, mentioning how it was used in the TV show Good Times, and how it represents African-American culture. Barack gets lunch for them, and they eat sandwiches in a park. Michelle insists on paying him for lunch since this is not a date. After, Barack offers her a slice of pie, saying that its the best, but Michelle doesn't like pie; she likes ice cream chocolate.
Barack is surprised that anyone could not like pie, but then says that he doesn't like ice cream, which surprises Michelle. He explains that he worked at a Baskin-Robbins as a youth and pretty much ate his fill of ice cream. Michelle is surprised that Hawaii has Baskin-Robbins, and Barack points out that it is one of the fifty states. They talk about Barack's background: how his white mother married his Kenyan father, but they separated shortly after his birth; how his father wasn't present for his childhood; how his father didn't finish anything in his life, and died in Kenya. Barack is obviously angry with his father. On the way to the community meeting, the topic of Michelle's frustration with the firm comes up again. Barack again suggests that Michelle isn't really upset with the firm, but this time, he goes further.
He says that Michelle isn't upset with the firm, since the firm is just doing exactly what it is supposed to do. Instead, he suggests that she is upset with herself for working at the firm instead of doing something more valuable for the community. He says that he knows she wants to do more important work, work that helps people, and that the real source of her frustration is that she has sold out working at the corporate firm. Michelle replies angrily that he is guilty of the same sell-out: he's going to school at Harvard, and his internship is at the same corporate law firm. He is taken aback and apologizes. The two arrive at the community meeting, where Barack is greeted warmly by everyone. One woman sits next to Michelle and describes how her son wanted to be a sailor since he was young, but living on the south side of Chicago, that dream was nearly extinguished. But Barack, she says, would talk to her son about it every time he visited, acting as a father figure to the youth.
The woman proudly shows Michelle a picture of her son in a U. S. Sailors outfit, saying that he is in the Navy, visiting all sorts of places and living his dream because of Barack. The topic for the day is the failed attempt to get city approval and funding for a community center. Everyone is upset because they put in so much effort with nothing to show for it. The speaker, a young man and friend of Barack's, is having a hard time keeping the crowd together on the topic. Eventually, in near desperation, he gives the floor to Barack, who proceeds to mesmerize the crowd. He says that they have to keep working to figure out how to get what they want.
He says that there are city council members who want to help them, but asks why they don't. Eventually, someone in the audience suggests that maybe its because the city council members think the outcome is already determined, and they don't want to waste their time on a lost cause. Barack leaps on that idea and points out that the first speaker has funding commitments for the community center, which is more than they had when they first put in the proposal. He says that they have to look at the situation from the council members point of view, which is something that a good friend (he nods to Michelle) taught him just that day. When they leave the community meeting, Michelle accuses Barack of knowing that he would speak at the meeting, casting himself in a good light for their not a date. Barack admits that he had a good idea that he would be speaking, but laughs it off, and Michelle seems okay with it.
The two have dinner and discuss their history further, including their religious beliefs both profess to have no formal religion, but to be spiritual. Barack describes how he spent time in Indonesia with his mother before moving back to Hawaii to live with his grandparents. He admits to smoking a lot of marijuana in high school. He describes how he dated a white woman for two years in college, but says that when he went to meet her family, even though they were welcoming toward him, he just didn't see himself fitting in. Michelle describes how her grandfather was unwilling to go into debt to help finance her fathers education, so he didn't finish college and had to take a manual labor job, but rose through the ranks to become a supervisor. He now has MS (Multiple Sclerosis), which is one of the reasons why Michelle is living at home. The two go to see Spike Lees Do the Right Thing.
They both enjoy it greatly, sharing popcorn. During the pivotal scene where the police kill Radio Raheem, Michelle is startled and reflexively takes Barack's hand. On their way out, Barack stops to use the restroom, while Michelle walks outside. She runs into a partner from her law firm, who also saw the movie with his wife. He comments on how inappropriate it was for Mookie to start a riot, and Michelle blankly nods, furtively glancing into the theater, hoping Barack won't come out yet. But Barack arrives just then. Michelle awkwardly tries to explain that they are not on a date, but that they had a community meeting to go to and just happened to go to the movie together.
The partner again expresses his disapproval of Mookie's actions. Barack smoothly suggests that Mookie was actually trying to save Sal's life had he not directed the angry mobs violence toward the pizzeria, they would have turned on Sal himself, and likely killed him. The partner is impressed with Barack's insight and compliments him to both his wife and Michelle, and tells Michelle to be sure Barack has a positive experience at the firm. After the partner and his wife leave, Barack expresses his true opinion: that Mookie was simply angry. Michelle rounds on Barack and angrily tells him that this is exactly why she didn't want to go out with him. She says that on Monday morning, the two of them will be the talk of the firm, and her position there will be ruined. He lets her wind down and then agrees to take her home. On the way, he stops the car.
Shes puzzled until she sees him walk into an ice cream shop. He comes out with a chocolate cone her favorite and she gets out of the car and sits by him while she eats it in silence. Eventually, she allows that the ice cream is good, and asks him if he wants a taste. He agrees, and slowly leans in and kisses her. He then takes her home..