In 1977, Harry Burns, portrayed by Billy Crystal, and Sally Albright, played by Meg Ryan, embark on a lengthy car journey from the University of Chicago to start their new lives in New York City after graduation. During the ride, they engage in a thought-provoking discussion on whether men and women can maintain a platonic friendship without sexual tensions complicating things. They reluctantly conclude that it’s not feasible and, upon reaching their destination, part ways.
Fast forward to 1982, Harry and Sally surprisingly reconnect during a flight. At this point, Sally is in a relationship with Joe, while Harry is preparing to marry Helen. This time, Harry reiterates his belief that friendships between opposite sexes are challenging, even when both parties are involved with others. After their flight, they go their separate ways once again.
By 1987, life has brought new changes for both Harry and Sally. Sally confides in her friends, Marie and Alice, about her breakup with Joe. Meanwhile, Harry shares with his friend Jess that Helen has ended their relationship. The two meet again at a bookstore, leading to a dinner where they catch up on life’s ups and downs. In a surprising twist, Harry discovers he has developed a genuine friendship with Sally. They start engaging in late-night phone calls, passionately debating topics such as Casablanca and whether Ingrid Bergman should have chosen Humphrey Bogart. As they spend more time together, they visit museums and delve deeper into each other's lives. However, Sally feels uneasy about revealing that she is dating again, but Harry encourages her to be open about it. During a particularly memorable dinner, Sally demonstrates her ability to fake an orgasm, leading to a humorous moment when another diner, a character played by Estelle Reiner, quips about wanting "what she's having."
As time passes, Harry attempts to pair Sally with Jesse, while Sally seeks to match Harry with Marie, resulting in an unexpected romance between Marie and Jesse. Roughly four months later, while shopping for gifts for Jesse and Marie’s wedding, Harry and Sally unexpectedly encounter Harry’s ex-wife. The plot thickens as Sally is now dating Julian, and Harry has been seeing Emily. However, when Sally learns that her former boyfriend, Joe, is tying the knot, she reaches out to Harry late at night for consolation. This night of comfort escalates when they share an intimate moment.
Uncertain about how to navigate this new dynamic, their relationship begins to distance. The tensions boil over during Jesse and Marie's wedding, leading to an argument. Yet, amidst these trials, on New Year’s Eve, Harry reaches out to Sally with a heartfelt declaration of love. In a moment brimming with emotion, they kiss, culminating in their decision to marry.
