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.”

Jesse

• Published in Film & TV
• October 29, 2024

Billy Crystal has a knack for storytelling. Whether it’s about a Hollywood set or a royal balcony, he always spins a tale that’s equal parts hilarious and memorable. 

Recently, the iconic comedian dropped a royal gem on “The View” that had audiences in stitches — a quirky ‘what if’ scenario with none other than the late Princess Diana.

Picture this: it’s 1989, and Crystal is seated with Princess Diana at the London premiere of When Harry Met Sally. There he is, alongside director Rob Reiner and the film’s star Meg Ryan, basking in the glamour of the evening. 

Crystal, who’s used to getting laughs, probably didn’t anticipate the reactions his movie would elicit from his royal guest, especially when that scene came up. 

Yes, we’re talking about the infamous Katz's Deli moment where Ryan’s character, Sally, loudly and unabashedly demonstrates to Harry that, yes, women can fake it. Cue audience anticipation.

This wasn’t just any night, and as Crystal hinted, the Princess’s reaction to that scene was one for the ages. Let’s just say Crystal left the theater with a memory he’d never forget — and a reason he might take a hard pass if there were ever a second “date” with the Princess store.

Billy Crystal dishes on his royal encounter with Princess Diana—and why it left a lasting impression.

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

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. 

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

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

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.

Jesse