Three years after they were first spotted together in 2011, the pair briefly split in 2014 before rekindling their romance two years later. They announced their engagement in 2018.
“I’m engaged at 67 to a very funny woman. Funniest woman I’ve ever met,” the “Jack & Diane” crooner — who is a father of five children, including Real Housewives of Beverly Hills alum Teddi Mellencamp — gushed in December 2018 of his then-fiancée. “One can well imagine, I’m probably not the easiest guy to get along with. So let’s leave it at that.”
Ryan, for her part, opened up about what drew her to the Indiana native during an interview with The New York Times later that same month — but confessed that romantic relationships felt “alien” to her.
“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,” she shared. “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.”
Ryan — who adopted daughter Daisy in 2004 — eventually called off the engagement in 2019, with a source exclusively telling Us Weekly that the When Harry Met Sally star had “no regrets” about her decision to end things with the “Small Town” artist. John, meanwhile, gave a glimpse into what went wrong between the pair while talking to Esquire four years later.
“I love Meg Ryan. I went with her for 10 years. She doesn’t love me so much. She’s a great girl. I’m just a s—y boyfriend,” he told the outlet in June 2023. He added that while the twosome got together when they were both first “coming out of [their] shells,” Ryan “learned how to do everything” while he “learned to do nothing.”
The Sleepless in Seattle star was no stranger to rocky relationships. Prior to her dating the Grammy winner, Ryan tied the knot with Dennis Quaid. The twosome — who share son Jack — were married for nine years but divorced in 2001 amid her affair with Russell Crowe.
“I think what divorce does is, it takes away your identity,” Quaid told The Sunday Times in 2018 while looking back on his marriage to the City of Angels star. “It’s like death. Your identity is wrapped up in the relationship and if it’s not going to be there … who are you? … Aren’t the most stressful things in life meant to be the death of a family member and moving house? And then there’s divorce, which is death and moving.”
Ryan, meanwhile, got candid about facing life in the spotlight after her failed marriage made headlines. During a 2003 interview with InStyle, she claimed that the A Beautiful Mind actor didn’t “break up” her marriage — and that Quaid had also cheated while the pair were together.
“Dennis was not faithful to me for a long time, and that was very painful,” she told the outlet. “I found out more about that once I was divorced.”
John, for his part, was married three times before meeting Ryan. He wed pregnant girlfriend Priscilla Esterline in 1970, and the twosome welcomed daughter Michelle six months later. After divorcing Esterline in 1981, the Grammy winner tied the knot with Victoria Granucci — with whom he later welcomed daughters Teddi and Justice — but they called it quits in 1989. He also shares two sons, Hud and Speck, with third wife Elaine Irwin, whom he wed in 1992. The pair split in 2010 after nearly two decades of marriage.
During an interview with Howard Stern in March 2017, John got candid about why his previous relationships have failed over the years — Ryan in particular.
“I think it’s because I’m a child. I throw fits, I gripe, I complain. I’m moody,” he explained. “Every bad thing that a fella can be, that’s me. … [Meg] just doesn’t want anything to do with me. And I can’t blame her.”
Keep scrolling for Ryan and John’s complete relationship timeline: