Of course, movie lovers all know what happened next: Ryan chose the latter, which proved to not only be a fateful decision for her career—When Harry Met Sally turned her into one of the world's biggest movie stars—but for another star's as well, with fellow romantic comedy queen Julia Roberts taking over her part in Steel Magnolias.
When Harry Met Sally was the first of many romantic comedies Ryan would front, with audiences unable to resist her comedic timing and charming personality. And, after a 14-year hiatus from the genre she helped elevate, Ryan returned to the rom-com world in this year's What Happens Later, which the 62-year-old also directed.
Not that Ryan considers the movie, which pairs her with David Duchovny as exes who unexpectedly reunite at the airport, a conventional romantic comedy. Rather, she described it as a "love story."
"These characters are in their 50s. It's a different story than when you're in your 20s," she told Glamour. "I wanted to make something beautiful and offer a new way of thinking about what love is."
It was a fitting endeavor for an actress who largely shaped how a generation of moviegoers view romance, thanks to her work in some of cinema's most iconic feel-good films. Some of them, of course, were written and/or directed by Nora Ephron, with Ryan dedicating What Happens Later to the legendary filmmaker who passed away in 2012.
"I believe in comfort movies," Ryan said. "In the movies I did with Nora, the characters lead separate lives, but whatever was happening, they were destined to find one another. There's a comfort in the kismet and the idea of an inevitable connection. It's a wonderland idea. It's an enchanted idea."
And What Happens Later proved Ryan is still as charming as ever. But how does her latest movie stack up against the eight other rom-coms she's starred in?
Get ready to have some thoughts because we ranked all of Ryan's rom-coms: