Love Story by Erich Segal is a timeless story of tragic love. Oliver is a child of privilege, the son of a family of importance dating back many generations. Jennifer is the only child of a widowed baker, as opposite from Oliver as one person can be. However, their union is one of strength and volatility that sweeps them both up in an uncontrolled wave, their love surviving every obstacle except one, mortality. Love Story is the Romeo and Juliet of the twentieth century.

Oliver meets Jennifer at the library on the Radcliffe campus. Oliver prefers this library to the one at Harvard, because the required reading material is much easier to find. However, Jennifer, the clerk on duty one fateful night, disagrees with Oliver's preferences and feels free to tell him so. This encounter leads to coffee, which in turn leads to a date to one of Oliver's hockey games. Oliver tries to convince himself that he does not like this opinionated girl, who does not even know who he is, let alone how prestigious his family is, while Jennifer attempts to convince Oliver she could not care less about his family or his impressive athletic abilities. However, neither is very good at convincing the other of anything but their joy in spending time together.

It is not long before Oliver and Jennifer are spending every free moment together. Oliver feels different with Jennifer, afraid to use his normal lines on her for fear she will see through him. Jennifer is different. Oliver does not want the same things from her that he has wanted from other girls. It does not take long before Oliver realizes the depth of his feelings for this girl.

Oliver has a strained relationship with his father, due to the fact that Oliver feels he can never compete with his father's accomplishments. Jenny sees this when Oliver takes her to meet his parents. Soon after, Oliver's father informs Oliver that if he marries Jenny, he will be cut off from the family fortune. Oliver takes this declaration as the severing of the relationship he has been waiting for. Oliver marries Jenny and begins his life separate from the Barrett legacy.

Oliver and Jennifer live on Jennifer's income for the three years that Oliver is in law school. During this time, Oliver and Jennifer find new ways to scrounge every day, making every penny stretch. Oliver's father attempts a peace offering by inviting Jennifer and Oliver to his sixtieth birthday party, but Oliver refuses to go. Unhappy with his decision, Jennifer argues with Oliver, until he explodes and throws the phone across the room. Jennifer rushes out of the apartment, and Oliver spends the rest of the night searching for her, finally finding her waiting on the top of the steps to their apartment.

Upon graduating from law school, Oliver receives many job offers. Finally, Oliver accepts a job with a law firm in New York City at a salary that is a record for a Harvard Law School graduate. Jennifer and Oliver enjoy their new wealth by buying every luxury they missed out on while living on Jennifer's teaching salary. Jennifer and Oliver also decide to try to have a baby. When Jennifer does not become pregnant right away, they go to a fertility doctor to rule out any problems. During the course of this investigation, the doctor discovers that Jennifer has a fatal type of leukemia. Oliver does not tell Jennifer at first, preferring to keep things as normal as possible. Jennifer, on the other hand, knows there is something wrong with her and goes to the doctor, insisting he tell her the truth.

Within weeks, Jennifer becomes so ill that she agrees to be placed in the hospital. Oliver stops going to work, preferring to be at Jennifer's side as often as she will allow. Oliver wants Jennifer to have everything she needs, so he goes to his father and asks for five thousand dollars without telling his father why. Jennifer's health declines quickly. Jennifer makes Oliver promise he will allow her father to have a Catholic funeral for her, just moments before she dies. When Oliver leaves the hospital after his wife's death, he finds his father rushing in. Oliver's father has just learned of Jennifer's illness and has come to support his son. Oliver allows himself to be consoled in his father's arms for the first time since he was a small child.