As the star of beloved romantic comedies like When Harry Met Sally . . ., Sleepless in Seattle and You’ve Got Mail, Meg Ryan was long known as “America’s Sweetheart,” and her charming screen presence is synonymous with witty banter and picture-perfect happy endings. Given her enduring onscreen association with romance, you might be curious about Ryan’s real-life loves. Here’s a look at her A-list relationships.
Meg Ryan & Dennis Quaid’s high-profile ’90s marriage
Meg Ryan and Dennis Quaid met during the filming of the 1987 sci-fi comedy Innerspace, and they started dating the next year, when they costarred in the 1988 thriller D.O.A. When they first got together, Quaid was the bigger star, but by the time they married in 1991, Ryan was one of Hollywood’s most in-demand actresses. Prior to getting with Quaid, Ryan dated her Top Gun costar Anthony Edwards in 1986.
Ryan and Quaid’s son, Jack, was born in 1992, and he’s now an accomplished actor with roles in movies like Scream (2022), Oppenheimer (2023) and Companion (2025) and shows like The Boys (2019 to present).
While Meg Ryan and her husband Dennis Quaid were one of the most famous couples of the ’90s, their marriage didn’t last, and their divorce, which was finalized in 2001, was the subject of much tabloid coverage. Tensions had been arising in their relationship for years due to Ryan’s rapidly rising fame and Quaid’s battle with drug addiction.
Reflecting on his marriage in 2024, Quaid said that when it came to Ryan’s newfound stardom, “I tried to be a big person and tell myself that didn’t bother me, but people are human,” adding, “She was ascending as I went into rehab and Meg is really such a great, sweet person and really talented and deserved all her success. But I don’t regret anything about my marriage to Meg, and we got Jack Quaid out of it who is really going on to maybe eclipse both of us.”
When asked about her divorce in 2000, Ryan said, “My marriage and the dissolution of my marriage . . . well, the real reasons for it will always be speculation, because I’ll never talk about what went down, and neither will Dennis. It dissolved before it became sport for the press.”
While Ryan originally said, “We both behaved very honorably—in our marriage and in our breakup. He never cheated on me,” shortly after her split, in 2008, she revealed, “Dennis was not faithful to me for a long time, and that was very painful. I found out more about that once I was divorced.”
Clearly, the end of Ryan and Quaid’s marriage was way more of a drama than a rom-com.
Meg Ryan & Russell Crowe’s scandalous romance
Ryan began seeing Russell Crowe, her costar in the 2000 film Proof of Life, as her marriage was ending. After her divorce, there was a lot of gossip about Crowe and Meg Ryan dating, and the media branded her a cheater, which hurt her career given her wholesome image.
The director of Proof of Life, Taylor Hackford, even claimed that their affair was directly responsible for the film flopping at the box office. In the early ’00s, Ryan ended up taking a step away from the spotlight, and she chose to take on darker roles once she returned to the screen.
When asked whether her relationship with Crowe led to her divorce, Ryan said, “Russell didn’t break up the marriage. He was definitely there at the end, but it wasn’t his fault.” She also said she was seen as “a scarlet woman” when she was with Crowe, but claimed, “As painful as it was, it was also incredibly liberating. I didn’t have to care about what people thought.”
In a 2019 New York Times interview, Ryan said that when she was dating Crowe, “I remember letting go of needing to correct anybody. Divorce is hard. Love is hard. All those things were so personal. They weren’t for mass consumption.”
Ryan also admitted that her short-lived relationship didn’t end well, saying, “I was a mess. I hurt him, too, at the end. I couldn’t be in another long relationship, it wasn’t the time for that. So I got out.”
Despite all the chaos around their affair, Crowe said, “Meg is a beautiful and courageous woman. I grieve the loss of her companionship, but I haven’t lost her friendship.”
Meg Ryan’s broken engagement with John Mellencamp
In 2006, while she was single, the Addicted to Love star adopted her daughter, Daisy. In 2010, Ryan embarked on a new high-profile relationship when she began dating musician John Mellencamp. Ryan and Mellencamp broke up in 2014, but got back together in 2017, and announced their engagement the next year. In 2019, they called their engagement off and split up for good.
In a 2023 Esquire interview, the “Jack & Diane” singer admitted, “I love Meg Ryan. I went with her for ten years. She doesn’t love me so much. She’s a great girl. I’m just a s–tty boyfriend.”
During her engagement, Ryan, who went on to direct the 2023 rom-com What Happens Later, in which she costarred with fellow ’90s icon David Duchovny, said, “What’s great about now is that John and I are so free to have fun. Maybe that freedom is about being a million years old. But I sometimes think relationships are for aliens. Who does it? Who can do it? I don’t know how any of us ever do.”
In recent years, Ryan hasn’t publicly stepped out with anyone, though in 2023, she told Glamour that dating was “just as ridiculous as ever,” saying, “I don’t think anyone ever gets good at it. Maybe people do. I don’t.” Even if Ryan thinks dating is ridiculous, we still can’t get enough of her love life, whether it’s in a movie or IRL.
