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Dexter and Emma spend the night together following their graduation from Edinburgh University in 1988. They talk about how they will be once they are 40. While they do not become romantically involved completely, this is the beginning of their friendship. The novel visits their lives and their relationship on July 15 in successive years in each chapter for 20 years. Emma wants to improve the world and begins writing and performing plays, which remain unsuccessful, while Dexter travels through the world, drinking and hooking up with women. Eventually both move to London where Emma becomes a waitress in Kentish Town at a Tex-Mex restaurant, while Dexter becomes a successful television presenter.

While there are various attempts from both sides to start a relationship, coincidences stop Emma and Dexter from getting together and while they have relationships with other people, they stay best friends, both secretly longing for the other. They are drawn together closer through a holiday together and the death of Dexter's mother.

Emma breaks up with her boyfriend, Ian, after realising she is creating a life with someone she doesn't love. During this time Emma is able to find a job as a teacher, after various years of struggle, despite a "double-first degree". Dexter meanwhile develops a drinking and drug problem and watches his career collapse. The friendship between Emma and Dexter grows more and more difficult, after Emma is constantly hurt by Dexter who attempts to hide his feelings for her from both her and himself. After being treated rudely by Dexter at a restaurant, Emma breaks up the friendship.

At the wedding of Emma's former roommate, Emma and Dexter meet again. Emma admits that she wants Dexter back. At this point of time she has just ended an affair with her headmaster, Dexter has fallen in love with another woman, Sylvie, who is pregnant. At this reunion, he invites Emma to his wedding, who is disappointed by the situation.

Emma tries to overcomes her problems and begins to write, while Dexter is unemployed and overwhelmed by his role as a father. After realizing this, he and Emma for the first time have sex. They do not get together and Emma leaves to go to Paris in the hope of writing a successful novel. When Dexter visits her in Paris, he learns that she met someone and likes him and for the first time admits his feelings to her. After talking about their relationship, Emma chooses Dexter.

Emma and Dexter get married and are happy together, however Emma wants a child. The couple finds themselves frustrated by the failing attempts to have a child. Dexter however is able to open a deli-cafe and finds himself suddenly successful again. Emma gets her book published and becomes a successful childrens author. On the anniversary of the day they met after graduation and the day they got together, Emma and Dexter have an appointment to see a house. While travelling there, Emma has a bike accident and dies. After her death, Dexter finds himself in despair. He starts to drink again and provokes people in bars in order to get beaten. He is comforted through his ex-wife Sylvie, his father and his daughter. The upcoming year he travels together with his daughter to Edinburgh where he and Emma met and they climb the same mountain together that Emma and Dexter climbed 19 years ago