Meg Ryan on Aging, Dating, and Rom-Coms

One area Ryan admits hasn’t gotten easier with age is dating. Ryan ended her engagement to musician John Mellencamp in 2019, but even the queen of rom-coms has something to learn about navigating romantic relationships. “It’s just as ridiculous as ever,” she says with a laugh and a classic Meg Ryan hair toss. “I don’t think anyone ever gets good at it. Maybe people do. I don’t.” Surely she’s improved since her worst date, though. “I went on a date in college where he took me on a motorcycle ride all over northern Connecticut and Massachusetts. It was great. We ended up having dinner, and when we rode back to my dorm room, I was like, ‘I had the greatest time, Phil.’ And his name was something like Bob. I never heard from him again. I had it all wrong, but it was fun.”

In 1989, When Harry Met Sally tackled the age-old question: Can men and women ever just be friends? And 34 years later, a quick Google search will show that it’s still a hot debate. But for Ryan, there’s no question. “Yes, I think they can be friends,” she says. “I have really great male friends and I love their perspective. I see their confusion right now with the shifting roles and I feel their desire to do it right, to get better. I have a lot of empathy and respect for that.”

Speaking of When Harry Met Sally, it wasn’t Ryan’s first film but it was the one that arguably catapulted her to fame and cemented her status as America’s sweetheart. “There are worse things to be called,” she says. It was also her first time working with the late Nora Ephron, who wrote the script. The two would go on to collaborate on a number of projects including, of course, Sleepless in Seattle and You’ve Got Mail, two movies that perfectly captured the internal monologues women were having at the time about love, sex, and our place in the world. “I believe in comfort movies,” Ryan says. “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.”