Trama

The movie is framed with stories of elderly couples telling stories about their relationships. Several stories are told throughout the movie. A couple talks about how they fell in love at first sight and knew that they were going to spend their lives together. Another one says how they met 30 odd years after 6th grade and got married shortly after. In another case, the guy got married and divorced a few times before he met the woman of her dreams. The point being that there is no set template for the "happily ever after" and that each love story follows its own path.

The story begins in 1977. Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) finish college at the University of Chicago and meet when both need someone to share a drive to New York City, where Sally is beginning journalism school and Harry is presumably starting a career; at the time, Harry is dating a friend of Sally's, Amanda (Michelle Nicastro). Harry irritates Sally from the beginning as he won't stop smooching Amanda, even though Sally was waiting in the car for him.

The underlying theme arises from their differing ideas about relationships between men and women which emerge during this journey. Sally is super organized and disciplined and Harry is none of those things. Sally wanted to divide the 18-hour journey into 6 shifts of 3 hours each, or by mileage.

Harry says that journalism is a profession where one only writes about things that happen to other people. Sally is a happy person, while Harry characterizes himself as the dark one. He claims to read the last page of the novel first, so in case he dies before he finishes it, he knows how it ends.

Sally says that women are practical, while Harry believes that a passionate marriage is better than the "right" one. They have a meal at a diner and Sally is a fussy person who likes her order with a lot of conditions. Harry guesses correctly that she is broken up with her boyfriend, which she claims is due to jealousy.

Harry calls Sally attractive and she is offended as she thinks Harry is coming on to her, as he is dating Amanda. Sally says that they will only ever be friends. Harry evinces the view that "Men and women can't be friends because the sex part always gets in the way" even with ones "he finds unattractive". Sally disagrees, claiming that men and women can be strictly friends without sex. On the way, at a stop in a diner, Sally is angered when Harry tells her she is attractive; she accuses him of making a pass at her. In New York, due to their divergent philosophies, they part on less than friendly terms.

Five years later, they meet in a New York airport and find themselves on the same plane. Both are in relationships; Sally has just started dating a man named Joe (Steven Ford)-who happens to be an old friend of Harry's-and Harry is engaged to a woman named Helen (Harley Kozak), which surprises Sally. Sally is a journalist now. Harry was sitting behind Sally and exchanged seats with the person sitting next to her. Harry postulates that women like to hold on to men all night after sex, and men are thinking if 30 seconds are enough for them to get out of bed and go back to their own home.

Harry suggests they become friends, forcing him to elaborate on his previous rule about male-female friendships; they can never be friends because the sex part gets in the way by suggesting an amendment that they can be friends if both of them are in separate relationships. But Harry also that seeking a friendship outside the relationship can mean that the relationship is missing something and is eventually doomed for failure. Despite Harry's suggestions of exceptions to that rule, they separate concluding that they will not be friends.

Harry and Sally meet yet again five years later, in a New York bookstore. They have coffee together and talk about their previous relationships, which have ended. Sally broke up with Joe just a few weeks ago. She is 31 and is under a lot of pressure to get married and start a relationship. Harry was married but found that his wife was cheating on him. Harry is a political consultant.

After leaving the cafe, they take a walk and decide to be friends. In subsequent weeks, they have late-night phone conversations, go to dinner, and spend a lot of time together. Their dating experiences with others continue to highlight their different approaches to relationships and sex.

During a New Year's Eve party, Harry and Sally find themselves attracted to each other. Though they remain friends, they set each other up with their respective best friends, Marie (Carrie Fisher) and Jess (Bruno Kirby). The four go to a restaurant, where Marie and Jess hit it off; they later get engaged.

One night, Sally tearfully tells Harry over the phone that her ex, Joe (Steven Ford), is getting married to his legal assistant, and he rushes to her apartment to comfort her. They unexpectedly have sex that night, resulting in an awkward moment the next morning as Harry quickly leaves in a state of distress. This creates tension in their relationship. Their friendship cools for three weeks until the two have a heated argument during Jess and Marie's wedding dinner. Following this fight, Harry repeatedly attempts to mend his friendship with Sally.

At a 1988 New Year's Eve party with Jess and Marie, Sally misses Harry. He is spending New Year's Eve at home, watching Dick Clark's 16th annual New Year's Rockin' Eve. Before midnight, Harry walks around the city. As Sally is about to leave the party, Harry appears and declares his love for her. She claims he is only there because he is lonely, but he lists the many reasons he loves her. Harry and Sally marry three months later, exactly 12 years and three months after their first meeting.

The last segment in which couples discuss their relationship histories is an interview with Harry and Sally, talking about their wedding.