Getting Cozy With Meg Ryan

Meg Ryan is not having a very Meg Ryan fall. Instead of curling up with a good book, an even better sweater, and a steaming cup of tea, Ryan has spent the last few months flying back and forth between New York and Los Angeles for a planned-to-the-second schedule created by a team of publicists and managers to promote her new film, What Happens Later. It has not been very cozy.

She’s done the Today show and Entertainment Tonight. She’s sat down with Jimmy Kimmel, Seth Meyers, and Kelly Clarkson. She’s done photo shoots for this very magazine, for People, and for The New York Times. She attended a film screening at Lincoln Center. All in a day’s work for one of the most recognizable actors on the planet, but when you’ve been out of the spotlight for eight years—and you’re not only starring in a new movie but also directed and cowrote it—let’s just say the oat milk cappuccino she orders during our interview at New York City’s iconic Carlyle hotel is very necessary.

These are just a few sentiments expressed to me when I casually told friends and colleagues I’d be interviewing Meg Ryan:

“I’m so obsessed with her.”

“I literally watch When Harry Met Sally every year.”

“You’ve Got Mail made me want to move to New York.”

“I still bring photos of her shag to my hairdresser.”

These sentiments I believe act as proxies for how most women of a certain age feel about Ryan’s place in the pantheon of pop culture. More than three decades after they defined a genre, the golden trifecta of 1989’s When Harry Met Sally, 1993’s Sleepless in Seattle, and 1998’s You’ve Got Mail—still three of the highest-grossing romantic comedies of all time—remain canon. They’re our go-tos for heartbreak, sick days, and times when we want to remember that our lives weren’t always consumed by dating apps, cable news, and follower counts. Times when chatting with an online stranger during the internet’s early days was adorable and not at all creepy. Times when phrases like I’ll have what she’s having felt delightfully subversive and a little naughty. Times when we learned we could find our happily ever after and perfect knitwear.

Admittedly, it’s difficult not to think of Ryan as that same effervescent, button-nosed, intentionally messy-haired ingenue whom America crowned its sweetheart for almost a decade. But the truth is the 62-year-old’s career has been varied and prolific, with roles in 1991’s biopic The Doors, 1997’s dark comedy Addicted to Love, and 2003’s psychological thriller In the Cut—and she’s quick to point that out.

“What I had in the ’90s was a ride,” she says, sitting across from me at the Carlyle dressed in a black-and-white-striped sweater, black pants, and Dansko clogs. “It was a kind of moonshot and was really fun, but it’s just one ride out of the billions of things you could be interested in.”

Some of those billions of things, for Ryan, include spending time with her children, Jack, 31, and Daisy, 18, traveling, writing, renovating her Santa Barbara house, and generally “hanging around.” Things that made her eight years outside the industry highly fulfilling. So fulfilling that she wasn’t actively looking to return to work in the traditional sense. But when she was quarantined during COVID, Ryan received a draft of the What Happens Later script, which was based on Steven Dietz’s 2009 stage play Shooting Star and is available now on demand. The story follows two exes, Willa and Bill, who reconnect after 25 years while stranded in an airport during an epic storm. It struck a chord. “I had moved to a new town with my daughter right before the pandemic, and I remember really craving connection,” she says. “We were in isolation, and I read this script about being locked down with a person you had unresolved issues with. Would you take the opportunity to resolve them? It was an easy thing to imagine.”

Shooting took place between a mostly empty airport and a museum, and—despite its modest $3 million budget—resulted in a charming two-hander that stars David Duchovny as Bill, Ryan as Willa, and an unseen narrator as the only other voice we hear. Ryan says she has “forever affection” for Duchovny after working with him for the first time: “To watch how David could straddle a moment and make you laugh and feel terrible at the same time just takes such a specific intelligence.” And he feels the same. “Meg is disarmingly humble about herself,” says Duchovny. “I feel lucky that she chose me to do this film with her.”

What Happens Later, Ryan says, is a love story, not a romantic comedy, which might surprise those who associate her with the genre that put her on the map. “These characters are in their 50s. It’s a different story than when you’re in your 20s,” she says. “I wanted to make something beautiful and offer a new way of thinking about what love is.”

In cowriting the script, Ryan reworked Willa’s storyline to make it more personal, incorporating an emotional scene in which the character shares that she gave up a baby for adoption but thinks her child found loving parents. Ryan herself adopted her daughter from China in 2006 at around two years old. “I put that in there because my daughter is my daughter,” she says. “I’m convinced of magic because of our relationship. We were destined.”

Unlike most actors who instantly put up privacy guardrails when asked about their family, Ryan beams with pride when the subject of her kids comes up, and it’s clear that this whole interview could be derailed—in the best way possible—by pivoting from Meg Ryan, movie star, to Meg Ryan, mom. “My kids have always been a blast. They’re the best hang,” she says. “They’re so alive in their curiosity and interest in the world.”

Daisy and Ryan spend their time watching classic movies together, such as The Philadelphia Story, Bringing Up Baby, and It’s a Wonderful Life. Ryan’s past films, though, are not on their must-watch list. “I think she’s seen one. She’s blissfully unaware of all of it,” the actor says. Ryan lights up when talking about Daisy’s first year in college—how she wants to take more credits than she’s supposed to, how her hobbies include designing, sewing, and tailoring, and how she’s even exceptionally hemmed pieces from Ryan’s own closet. “I’m just so happy to know them, to be their mom,” she declares.

Jack Quaid, Ryan’s 31-year-old son with ex-husband Dennis Quaid, is an actor in his own right, currently starring in the Amazon hit action series The Boys. “I remember seeing him in a middle school production of A Midsummer Night’s Dream,” she says. “He was playing Bottom. I was newly divorced from his dad, and he was seated at the other side of the gym. I had my head in my hands and was like, ‘Oh, no. He’s good. He’s really good.’ I leaned forward, and I see Dennis, and he’s also leaning forward with his head in his hands. I just knew.”

Part of the dismay in realizing Jack’s talents, she says, was knowing the rejections and unwarranted cruel scrutiny that come with a career in the public eye—aspects of the job that Ryan has dealt with herself for years. “You don’t wish it [on anyone]. It’s too hard and it’s too weird,” Ryan says. “Jack is really talented. He’s more of a natural than I’ll ever be. That nepo stuff is so dismissive of his work ethic, his gifts, and how sensitive he is to the idea of his privilege.”

Jack is now just about the same age Ryan was when she starred in Sleepless in Seattle. “Our culture is so obsessed with youth,” she says, nodding at the fact that Hollywood almost never features women over 50 in anything more than supporting roles onscreen—let alone the romantic lead. “As an old person now, I love my age. I love where I’m at,” she says. “Aging is not that terrifying. We’re all doing it. I wish someone had told me earlier, ‘Just relax. It is what it is. Don’t pay attention to the obstacles.’”

Part of Ryan’s confidence is the result of her own self-protection, having learned to block out the incessant tabloid obsession with everything from her looks to her relationships. She’s been called “unrecognizable,” and her “rare” public appearances have sent corners of the internet into a tailspin. It would be too much for anybody to take. “I can’t pay attention to it. I just can’t,” she says of gossip culture. “It’s not worth it. Of course that would hurt someone’s feelings, but there are so many more interesting things to think about. Meanness and hatred are just so stupid.”

Getting older for Ryan has also meant no longer trying to please, and being unapologetically herself. “There’s a time in your teens and 20s where you’re trying on personalities to figure out who you are, who to be,” she says. “With age, you get to a place where you say what you mean without thinking about how it’s going to land. You just say what you want.”

Like us all, she’s still a work in progress. When I bring up a 2019 interview with The New York Times Magazine in which Ryan said that when she was coming up in Hollywood, she could never be sexy, she counters her remarks: “I don’t think I agree with that. I think I’m sexy enough. I was beating myself up. It wasn’t very nice of me.”

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.”

What Happens Later is dedicated to Ephron, who passed away in 2012. “It was such a no-brainer,” she says of the “For Nora” script that sweeps across the screen as the credits roll. “I have a lot of blessings in my life, and I have to say that Nora’s responsible for a lot of them. Of the few movies I did with her out of the 40 or so I’ve done, those are the ones that people associate me with.” Ryan remembers her first impression of Ephron well: “She was super expressive with her hands. You could tell she was a writer.”

Being a part of Ephron’s world meant dinner parties in her corner apartment on New York's Upper West Side that you’d never want to leave, with everybody switching seats at dessert. Her film sets were similarly joyful and fun, and included cherry pie taste-offs for good measure. “A few years after she died, I was looking for an apartment in New York City, and [the real estate agent] took me to hers without telling me,” Ryan says. “They didn’t know. I went into her apartment and it was empty. It was so intense. I couldn’t believe it. My memory was so alive and giant, but this was not. It’s just amazing how much life she brought into a place.”

Ryan can pinpoint the exact moment in her life when she realized she was not just the Meg Ryan she had always known but something else entirely: Meg Ryan the famous person. It was not something she ever sought out or particularly desired. She was acting in the soap opera As the World Turns to make extra money while studying journalism at New York University and took the train to Connecticut to visit her grandfather. “Everyone was talking to me like they knew me,” she recalls. “I was like, Oh, my God. I couldn’t believe the number of women giving advice for my character. I had always taken the train, but then suddenly I was in people’s houses and famous. It was weird, like a smash cut to that moment.”

“You can see the focus on notoriety and fame to be considered a power, and it isn’t,” she says. “Be careful what you want.” Despite her understandable allergy to fame, Ryan recognizes the impact her work has had on women. “I’m really happy if they connect with my characters,” she says. “I have had such an amazing, amazing embrace.”

And just like that, it’s time for Ryan to leave our coffee. She has Late Night With Seth Meyers to prep for. We embrace, and Ryan heads out of the hotel restaurant, publicist in tow, but not before a table of 30-something women interrupt their buttoned-up working lunch, heads craned, to giddily stage whisper: “Oh, my God, that was Meg Ryan.”

Caitlin Brody is Glamour's global entertainment director. Follow her at @cbroday.

Photographed by Shaniqwa Jarvis

Styling: Carolina Orrico

Hair: Derrick Spruill

Makeup: Jo Strettell

Manicure: Emi Kudo

Set design:  Kelly Infield

On-set production:  Ilona Klaver

Originally Appeared on Glamour