Billy Crystal Says Princess Diana ‘Ruined’ Their Chances At Romance After Her Unexpected Reaction To Meg Ryan’s Famous Scene
“Let’s just say, if we were dating, I wouldn’t see her again.”
Billy Crystal thought he was headed for a normal night at the theater, then Princess Diana sat right next to him and somehow turned a movie moment into a full-blown “romance killer” story.
Here’s the setup: Crystal was positioned beside Diana while Meg Ryan was just a seat away, and the whole balcony crowd was buzzing before the infamous deli scene even started. When Ryan’s character went full throttle with that legendary bit, everyone in the packed theater turned to see what the British royal would do. Diana’s response was not subtle, not polite, and definitely not what anyone expected.
Crystal swears that one hearty, echoing laugh changed the mood, and maybe his chances, forever.
Billy Crystal dishes on his royal encounter with Princess Diana—and why it left a lasting impression.
Getty ImagesThat’s when the theater’s energy went from “movie night” to “everyone holding their breath,” especially with Diana sitting right beside Billy Crystal during Ryan’s famous deli scene.
Recalling more about the evening, Crystal said he was positioned directly beside Diana in the theater while Ryan was just a seat away. The atmosphere was electric, with trumpets sounding as they entered the balcony seating.
In the packed theater, as the infamous deli scene played, the crowd was as curious as ever. Crystal felt the tension as everyone — and he means everyone — turned to see how Princess Diana would react to Sally’s…enthusiastic demonstration.
When Hollywood royalty meets British royalty: Billy Crystal, Meg Ryan, and Princess Diana share a night to remember
Getty ImagesThe laugh hit, Diana let out that reverberating bark, and Crystal immediately joked it was the kind of sound that would make him avoid a second date.
The actor describes that the whole theater seemed to hold its breath, waiting for the royal response. And Diana’s reaction? Well, it was far from what anyone might have expected.
She let out a hearty, reverberating laugh that echoed throughout the halls. It was more like a bark, really. “The laugh. She’s beautiful, but the laugh!” he quipped.
He joked that this laugh, though endearing, might’ve kept him from asking her out on a second date had they been romantically inclined. In his words, “[It was] the kind of laugh that if we were dating, I wouldn’t see her again.”
He also added that though such a display was untraditional for a princess, it made the night unforgettable.
This royal movie moment is just one of many in the legacy of When Harry Met Sally, which not only marked a high point in Crystal’s career but also became an enduring classic.
Similar to the famous couples who survived fame and scandal, Crystal’s Diana moment stuck with him.
Billy Crystal and Meg Ryan captured hearts in 1989’s When Harry Met Sally — and they’re still the duo we can’t get enough of
Hulton Archive/Getty Images
Meanwhile, the crowd’s curiosity doubled down because Diana was basically the only person who could make a comedy moment feel like a royal event.
Director Rob Reiner has shared that Meg Ryan’s deli scene wasn’t easy to capture, often requiring multiple takes to get the right level of comedic exaggeration.
Crystal joked that he had to endure 27 pastrami sandwiches during filming, which he called “a lot” even for a New Yorker.
Meg Ryan’s performance was so epic, it had Princess Diana losing her royal etiquette
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Even the behind-the-scenes chaos for Meg Ryan’s deli scene, with all those takes and 27 pastrami sandwiches, makes Diana’s reaction feel even more unforgettable.
Despite his humorous qualms, Crystal reflects fondly on that night with Diana, reminding us that even a princess is susceptible to a good belly laugh. And as for Crystal? He's still got his comedic spark.
His latest project, Before, is set to premiere on Apple TV+ this October. But no matter how many roles he plays, we’ll always remember him as Harry—and that unforgettable date with Princess Diana.
Billy Crystal's anecdote about Princess Diana's unexpected reaction to Meg Ryan's famous scene highlights the intricate dance between celebrity culture and personal relationships. This moment serves as a reminder of how public figures can inadvertently shape the expectations and emotions surrounding romance. Crystal's humorous storytelling sheds light on the complexities that arise when personal interactions intersect with the public eye, particularly in a world that often romanticizes celebrity relationships.
The ability to critically analyze these portrayals allows audiences to navigate their own relationship dynamics more effectively. By reflecting on these celebrity narratives, individuals can cultivate a deeper understanding of their connections, ultimately fostering more authentic and fulfilling relationships. Open discussions about these themes can help dispel the unrealistic expectations that often accompany the glamour of Hollywood romances.
That laugh was so intense it didn’t just steal the scene, it stole Crystal’s romantic momentum too.
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