Princess Diana Wore the Most Gloriously '80s Dress to the Premiere of When Harry Met Sally

She called star Billy Crystal "naughty" during the London screening 30 years ago. 

It’s hard to believe that a romantic comedy as sharp and socially relevant as When Harry Met Sally came out 30 years ago, but one need not look past Meg Ryan’s tousled ‘do to know that the film was, in fact, a product of 1989.

Meg Ryan And Dennis Quaid
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The film’s premiere(s) brought out a slate of A-listers, some of whom have stood the test of time, others who haven’t (O.J. Simpson and Nicole Brown’s date night is off-putting in retrospect, to say the least).

Premiere of
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Maria Shriver, John Cusack, and Bruce Willis and Demi Moore all came out for the film’s L.A. premiere.

Ron Galella Archive - File Photos 2010
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Premiere of
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"When Harry Met Sally" Beverly Hills Premiere
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Months later, when the movie came to London, Ryan and co-star Billy Crystal made an incredibly high-profile fan: Princess Diana.

The late Princess of Wales arrived at the premiere in a bright red Bruce Oldfield gown with a silvery criss-cross pattern, ruched fabric at the hips, and voluminous short sleeves — i.e. the most ‘80s dress of all time. Adding to the era’s quintessential vibe, she rimmed her eyes with cobalt blue eyeliner.

Diana, Princess of Wales attend the Premiere of When Harry met Sally
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Diana, Princess of Wales attend the Premiere of When Harry met Sally
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In an exclusive interview with People for the film’s 30th anniversary, Crystal and director Rob Reiner opened up about what it was like to watch their film with the beloved royal.

Royal Family
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“All I’m thinking the entire time is, ‘How is she responding to this?'” Reiner recounted. “And now the orgasm scene is coming, I’m going ‘Oh God. Oh my God.'”

Crystal, who sat next to the princess, said, “The lights went down and she whispered to me, ‘I’m taking my shoes off.’ So I went, ‘I’m taking my pants off.’ And she goes, ‘Oh, you’re so naughty!'”

“She turned to Billy and says, ‘I’d be laughing a lot more, except I know everybody’s looking at me,'” Reiner shared. “And then she asked for the film at Buckingham Palace so she could watch it with her friends.”

One can only hope Buckingham Palace still owns a dusty VHS version of When Harry Met Sally.

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