For InStyle's 25th anniversary September issue, the 57-year-old actress reflects on her life since her first time covering the magazine back in 1997. In those 22 years, Ryan has raised two children, 15-year-old Daisy and 27-year-old Jack Quaid, gone through a public divorce with Jack's dad, Dennis Quad, and just last year, she got engaged to musician John Mellencamp. After all the ups and downs, Ryan is pretty content at this stage in her life, with her focus remaining on her family, work and happiness.
"I’m focused on producing. I’m also teeing myself up to direct, and I’m working on a fun e-commerce project with some of my friends. But most of all, what I’m ambitious for in the 12 hours a day that I’m awake is my kids' happiness. I just am," she tells the magazine. " I’m either figuring out how to provide for them, figuring out how to say it right, figuring out all those mom things. I want them to be happy."
As for when she plans on tying the knot with Mellencamp, Ryan notes, "And today I’m happy too. Yes, I’m going to get married at some point. But for now this engagement thing is a state of grace."
Ryan also shares with the magazine what she learned from her divorce from Quaid in 2001. By the time she was featured on her second InStyle cover in 2003, the Sleepless in Seattle star says that "all of my expectations about everything had been blown up," a fact she considers to be "a good thing."
"People think they should be this by the time they’re 20 and this by the time they’re 30 and accomplished by the time they’re 40," she notes. "I was in my early 40s at the time of the cover shoot. And I said in the interview that I thought assignment of age was arbitrary. I stand by that -- especially now when it’s all about pivoting, recreating, and having multiple careers."
Her third cover came in 2008, and, with it, still questions about if she was lovable.
"I said I had an inability to accept myself as lovable. That was harsh. I think it stemmed from starting over after my marriage ended. Divorce is hard," she recalls. "I wasn’t easy on myself around then. I retreated. But that tough time was necessary. I became a better person after all of that. And I grew up a lot."
Ryan previously opened up about her engagement to 67-year-old Mellencamp in a February interview with The New York Times Magazine.
"What’s great about now is that John and I are so free to have fun," Ryan said. "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."