Ever felt lonely on New Year’s Eve? Taken at its most wondrous ideal, December 31 lends itself to the romantics, to toasts with friends, to sealing hopes with a kiss. But it’s also a holiday of expectations, one where loneliness and yearning can seep into the edges amid the champagne bubbles and shiny balloons.

As 1987 turns to 1988, charming cynic Harry (Billy Crystal) and bright optimist Sally (Meg Ryan) dance and share an awkward peck, making a pact to spend the holiday together again next year if they’re both still single. As 1988 turns to 1989, they reminisce alone—until, twelve years since they first met and moments before the clock strikes midnight, he rushes to her side. Because, “When you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.”

With those words, director Rob Reiner and writer Nora Ephron’s pitch-perfect collaboration When Harry Met Sally… entered the pantheon of romantic comedy classics.

Ephron and Reiner had begun the project as recent divorcées (her from journalist Carl Bernstein, he from director Penny Marshall), but in the five years between the first draft and finished film, the collaborators discovered new perspectives. Ephron married GoodFellas co-writer Nick Pileggi in 1987, who she would be with for 25 years until her death. Reiner’s sentimental streak came at nearly the last minute. During the movie’s production, director of photography Barry Sonnenfeld introduced him to photographer Michele Singer, even predicting beforehand that the pair would get married. Crystal helped come up with the lines for the midnight confession, Harry and Sally got their happy ending and Reiner and Singer—still together today—tied the knot before the film even reached theaters.

It’s a testament to how When Harry Met Sally… draws so much warmth from the specificity of its real-life connections. Inspired by the behind-the-scenes anecdotes, I set out to hear from Letterboxd with their own deeply personal ties to the picture to ask what makes them return to it again and again. Within 24 hours, more than 50 devotees answered my call-out. Fittingly, what stood out the most was how in Harry and Sally, people see themselves and their relationships—romantic, platonic and familial alike.

Take Ana, who first became obsessed at age ten after her dad shared how the love story reflected him and her mom. “My dad prefers his blockbusters, while my mom indoctrinated me into the French New Wave since I was six. However, When Harry Met Sally… is one of those few films where they can meet in the middle, which is almost too perfect considering what it is about,” she shares. “They cannot help but tell the exact same stories about their own lives any time we sit down together for a rewatch. I know they know I’ve heard it all before, but they are still too glad to share them and I am still too glad to hear it.”

Twenty-year-old Caro celebrates every New Year’s Eve by watching the film with her mom, who first introduced her to it about five years ago. Ever since, she’s treasured the opportunity to share it with other people she loves. “During my first year of college, my roommate and I watched it while packing for winter break and we got the idea because she was eating some Mallomars. We still constantly quote, ‘You’re right, you’re right, I know you’re right,’ to each other,” she says. “For my most recent birthday, my only wish was that I could make all my friends sit down and watch it, and I’ve never been more proud than when half of them cried at the ending.”

Before the lunch orders even went off to the kitchen, he pitched Ephron on a film about a lawyer. She immediately said no. But with business formalities swept aside, the rhythms of the conversation gave way to something much more intriguing as the three discussed love, sex and relationships. Ever the journalist, Ephron prodded the men with questions about their bachelor lives, both fascinated and appalled by their responses.

Something was there, and so when the trio met up again, Reiner brought a new idea: What about a movie centered on a man and a woman who agree not to have sex for the sake of their friendship—and then have sex anyways? This time, Ephron said yes. More lunches and more conversations about the ways men and women didn’t understand each other followed, and the pair never shied away from lending their own quirks to their characters, like the hyper-precise nature of Sally’s dining orders and her journalism career. In many ways, Reiner spoke for Harry and Ephron for Sally, ensuring the perspectives stayed in balance. The characters’ respective best friends, Jess (Bruno Kirby) and Marie (an achingly lovely Carrie Fisher) round out the main cast.

Out of concern for their relationship, Reiner initially hesitated to cast Crystal, his real-life best bud since they played onscreen friends in All in the Family. Sound familiar? But in true romantic comedy fashion, sometimes the person you’re looking for is the one standing in front of you all along. The longtime friends loved to talk on the phone while watching the same television shows—“If we lived next door to each other, we’d be connected with two paper cups and a string,” Crystal once said—and again, into the script it went. Even the love stories featured in the interludes came from Ephron interviewing of the production company, then tinkering the material with Reiner to shoot with actors.

When Fernanda met Fabricio, she had already seen the film over 100 times. After first falling in love with it in the cinema, she watched it at least once a week on an old VHS tape for years, (“Like a baby watching their favorite movie,” she jokes) and recalls her twenty-year-old self’s excitement at sharing it with her new best friend. Fortunately, he loved it, too. Best friends for 30 years and a couple for 28, “we kind of know it by heart, and the quotes and situations have bled [into] our lives like they’re from a friend or relative,” she says. “Now that we’re getting older, rewatching it and seeing those old couples in the movie talking about love, about how they met… I don’t know, I feel so lucky that now we are beginning to relate to them, too.”

Perhaps no scene better exemplifies the “yes and” collaboration than Sally’s fake orgasm at Katz’s Delicatessen, now a pilgrimage for any When Harry Met Sally… fan visiting NYC. It started with Reiner turning the tables on Ephron and asking for her to share something men wouldn’t know about women. Her reply? “Women fake orgasms.” Ryan had the idea for Sally to actually act out a fake orgasm to show the overconfident Harry how easy a woman could fool him; Crystal supplied the kicker spoken by a patron at the next table and Reiner enlisted his mother, Estelle, to deliver the line, now exalted as one of AFI’s top movie quotes: “I’ll have what she’s having.”

By the era of When Harry Met Sally…, the classic screwball conception had fallen from favor, but the 1980s weren’t necessarily a rom-com drought either. The decade saw the rise of John Hughes’ teenybopper subgenre, and a trio of critically acclaimed NYC-set offerings even directly preceded the film’s 1989 release: Cher won her Oscar with 1987’s Moonstruck, and 1988 featured Best Picture nominee Working Girl (Nichols again!) and the vastly undersung Crossing Delancey. The genre was also changing: a frequent comparison, Annie Hall in 1977, started a shift toward romantic comedies more interested in internal rather than external obstacles—or, “analyzing romance”, as Ephron once put it. (I’ll just put a personal asterisk here and give a nod to Shawn’s review.)

Still, Crystal felt trepidation over how a lowkey romantic comedy in July would fare against heavy hitters like Indiana Jones and the Last Crusade and Batman. But after an initially small-scale release got word of mouth going, When Harry Met Sally… grossed $92.8 million in North America—not too shabby for a $16 million budget. By certain box office metrics, the film’s success largely kickstarted a true golden age of romantic comedy that spanned the 1990s through the early aughts. People’s hunger for enemies becoming lovers, and the long box-office tail of the genre, popped up again just this year with the success story of Glen Powell and Sydney Sweeney in Anyone But You.

Here, I’ll it the summertime release feels surprising, given that nearly everyone I talk to brings up a fall or New Year’s Eve viewing tradition. Or both, in Marissa’s case. “I used to hate New Year’s. There was so much pressure in starting off a new year right, and it always felt so daunting. But When Harry Met Sally… makes New Year’s feel like a vessel for opportunity, and it reminds me that change doesn’t have to be scary,” she reflects.

For the past three New Year’s Eves, McKenzie and her wife Rachel have timed things just right so that the midnight countdown synchronizes with real life, a tradition that began when Rachel proposed right after Harry’s speech. Now, the film feels intimately tied to their romance, “a symbol of this artform we love and enjoy together so much that it became a part of our story”, as McKenzie puts it. “It’s a movie about the love that grows from truly knowing someone, the love that comes from spending a lot of time with another person and knowing them better than they know themselves. It’s patient, it takes its time, it never feels rushed... With Rachel, I feel like we’ve been together my entire life, but also like we just met yesterday, while at the same time being excited for the years and years we have ahead of us.” Is that ‘Auld Lang Syne’ I hear?