When faced with the struggles of quarantine, I have mainly drawn comfort from the escapism of movies. Not just any movie sufficed when it came to my daily viewings, as serious dramas would often fail at improving my spirits, and post-apocalyptic movies seemed a bit too… real. It was the rom-com that served as the best option, as most conflicts were simply a matter of ‘will they get together in the end or won’t they’ set to a romantic soundtrack. None proved to be more effective than When Harry Met Sally, a beloved 1989 romantic comedy which transports the viewer to the streets of New York City as Harry Burns and Sally Albright find friendship in one another and, eventually, romance as well. Director Rob Reiner effectively translates Nora Ephron’s script to the screen, while Meg Ryan and Billy Crystal make the characters well-realized and realistic. 

One of the most intriguing things about the film is the way it is separated into various chapters of the characters’ lives over a period of about twelve years. Each time the story jumps forward multiple years, the characters are presented differently. Harry and Sally are first shown to the audience as characters who could not be less compatible with each other. Right out of college, they meet for the first time when taking a road trip from Chicago to New York, which is probably the least desirable situation when it comes to getting to know someone for the first time. Harry’s cynical nature actively combats Sally’s optimistic demeanor, causing the two to fight as though they have known each other for years. By the time they arrive in New York, the two have already had multiple arguments regarding sexual partners, Days-of-the-Week underpants, the ending of Casablanca, and whether or not men and women can be friends without the threat of romantic involvement. Their second meeting about five years later goes similarly, and their interaction consists mainly of arguments and disagreements until they go their separate ways, expecting—and hoping—to never see each other again. The third time they meet, the two have finally grown to the point where they are able to perceive each other as friends, creating a foundation for their romance as they spend more and more time with one another.

Ephron’s script provides great opportunity for comedic moments, from the famous scene in Katz’s Deli where Sally fakes an orgasm to the game of Pictionary where an entire party cannot figure out that Sally’s drawing was meant to represent the phrase “baby talk.” Ephron has also created multifaceted and complex characters with their various quirks, such as Sally’s convoluted style of ordering food and Harry’s habit of skipping to the last page of any book he starts reading. Reiner’s direction offers a simple presentation of the story at first viewing, while also including subtle creative choices to be noticed more upon multiple rewatches, such as the various moments when Harry and Sally parallel each other.

The film breaks up the different chapters of Harry and Sally’s relationship with documentary-style interviews of older couples describing how they got together. The natural demeanor and delivery of each of their stories make the viewer stop and wonder if these people are actually couples who have been married for several years. The dynamics of each couple are unique to them and their story, making them feel like characters that we could know in real life. Some involve one person telling the story while their partner sits, smiles, and nods while never saying a word. Others have the couple alternating between one another, sometimes with one partner looking to the other to fill in various information regarding their story—like when the wife knows the names of all of her husband’s past partners. One couple (my personal favorite) tells their respective sides of the story simultaneously, somehow talking over each other without interrupting the other in a way that creates a rhythm and makes the viewer think, “these are two people who were meant for one another.”

As someone who has never been to New York, I believe the movie captures the city in a way that makes it feel familiar. The film shows the city dressed in the different seasons as Harry and Sally’s friendship grows within the setting. While the winter is given its own montage of snowy scenery and joyful city goers getting into the Christmas spirit, it’s the sequences in autumn that provide the most pleasing setting. The vibrant oranges and reds of the trees in Central Park form a heavenly backdrop for Harry and Sally’s walks. The city truly takes on a life of its own and becomes more and more inviting towards the viewer, even to those who have yet to experience the city in person.

The clever title references not just when Harry first meets Sally, but the several times they meet afterwards. They meet different versions of each other, each brilliantly portrayed by Meg Ryan and Billy Crystal. Ryan’s Sally grows from the more uptight and naïve version from their first meeting to a person who has become looser and cleverer, without changing the key things that make her who she is. Billy Crystal’s Harry evolves from the hard, cynical college graduate who thinks that he knows everything there is to know about the world to a man who learns to recognize his own feelings for others and eventually embraces his love for Sally. The two are believable as friends as well as a couple. Seeing the way Crystal’s Harry looks at Sally with admiration makes his final declaration of love convincing as well as satisfying. Similarly, the warmth Ryan exudes as Sally grows as a person is all the more enjoyable to watch. The small supporting cast also adds to the overall viewing experience. Carrie Fisher’s performance as Sally’s friend Marie is incredibly charming while Bruno Kirby as Harry’s friend Jess is hilariously candid. 

Hearing the hype surrounding this film for so many years would probably cause viewers to come in with high expectations. After multiple rewatches, I would say each viewing offers a new layer of brilliance to the film, even for those who do not typically find enjoyment in the romantic comedy genre.