The Story Behind When Harry Met Sally's Lovely 'How We Met' Moments

Billy Crystal and Meg Ryan as Harry and Sally being interviewed in When Harry Met Sally...
(Image credit: Castle Rock Entertainment)

It has been a pretty good time to be a fan of When Harry Met Sally in the early days of 2025. The stars of the 1989 romantic comedy classic, Billy Crystal and Meg Ryan, reprised their titular roles in a Super Bowl ad for Hellmann’s Mayonnaise and, the following month, appeared at the 2025 Academy Awards together to present this year’s Best Picture Oscar winner, Anora. A couple of weeks later, I scored a VHS copy of the film, which is how I watched it for the first time in years.

This was also the first time I watched director Rob Reiner and writer Nora Ephron’s witty, thought-provoking masterpiece knowing an interesting behind-the-scenes fact that I actually think is one of the most fascinating and, especially, heartwarming details about When Harry Met Sally… Read on to learn all about it.

The couple from the first "How We Met" moment in When Harry Met Sally...

(Image credit: Castle Rock Entertainment)

The "How We Met" Stories Are Based In Fact

When Harry Met Sally… follows the evolving relationship between the two central characters from strangers who hate each other to platonic friends to passionate lovers over the course of 12 years. Placed in between those notable chapters in their lives are documentary-style scenes in which married couples recall how they met, the last of which features Harry and Sally telling their story. Excluding that final moment, each of the stories from these scenes is based in truth.

Reiner explains in a DVD featurette that, while these interstitials are performed by actors, the stories they tell were collected by Ephron, who interviewed real couples about their “meet-cutes” and incorporated the memories into her screenplay. Reiner got the idea for these sequences when he asked the father of his friend, Alan Horn, how he met "Mrs. Horn," and he immediately “lit up” at the opportunity to talk about it. The filmmaker then realized that everyone has a good story about how they met their spouse, which became the general basis for When Harry Met Sally...

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Rob Reiner as Marty Di Bergi interviewing the band This Is Spinal Tap

(Image credit: Embassy Pictures)

Making When Harry Met Sally… Is Rob Reiner's Own "How We Met" Story

Another fascinating detail about When Harry Met Sally… is that the film originally ended on a more heartbreaking note. Instead of their happily ever after, the rut in their friendship after an awkward one-night stand would prove ultimately irreparable. The reason, as Reiner revealed to CNN’s Chris Wallace, was that, after 10 years of the single life following his divorce from the late Penny Marshall, he could not imagine falling in love again.

Everything changed when he fell in love during the production of When Harry Met Sally… Reiner explained to James Corden on a 2016 episode of The Late Late Show that, after meeting his wife, Michele Singer, he and Ephron decided to give Harry and Sally the happy ending that audiences would come to cherish forever.

Reiner was certainly on to something when he realized that everyone has a good “how we met” story. He just didn’t realize that he was about to experience his own while making a movie based on that very concept. It is yet another reason why When Harry Met Sally… is one of the all-time most important movies about the mystery of love.

Jason Wiese
Content Writer

Jason Wiese writes feature stories for CinemaBlend. His occupation results from years dreaming of a filmmaking career, settling on a "professional film fan" career, studying journalism at Lindenwood University in St. Charles, MO (where he served as Culture Editor for its student-run print and online publications), and a brief stint of reviewing movies for fun. He would later continue that side-hustle of film criticism on TikTok (@wiesewisdom), where he posts videos on a semi-weekly basis. Look for his name in almost any article about Batman.

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