Rosie: It's why I wanted to be successful—to have enough money to have children, to give them a life I didn't have, and then to be done when I was 39 or 40, because that's about how old my mother was when she died.
Oprah: You thought that was going to be your fate, too?
Rosie: I did. I had the sense that there was some sort of predetermined time limit on me. And every year after that has felt like extended play. You know when you play a video game like Grand Prix—well, you probably don't know this, Oprah, but sometimes you get an extra lap. That's what I've felt every year since I turned 39. Like, Oh my God, I got another one! Oprah: You always knew you were going to be a parent, even when you were a little girl growing up on Long Island.
Rosie: From the beginning. When I was 6 years old, I was always the one holding babies. When I got to be 18 and could sit at the adult table, I chose to sit at the kid table. The truth is, I'm a little socially awkward—with adults, I still need Relationship 101. But I was always comfortable around kids and always wanted a family of my own. When I started my first show, I said, "I'm going to quit in five years," because that's when Parker, my oldest son, would have been entering kindergarten. I ended up extending it to six years, but I knew that was the finish point. Even though they said, "We'll give you this and that," I told them, "There's nothing you could give me that would make me stay." My kids were starting school—I wanted to be there for all the things my mother missed.
Oprah: Because at that point you really understood what she missed.
Rosie: When I first held Parker, it hit me the most. I was like, Oh my God, she felt this [puts her hand over heart]—and then she knew she was dying and leaving five children with a man who I think she realized was incapable in many ways. What that must have felt like for her...
Oprah: Is there a part of you that's not in full gear for life because you're expecting not to make it?
Rosie: The opposite—I'm always in high gear because I know it could end at any moment. I'm trying to absorb everything—to the point where for a while I was really overdoing photos of my children. I just wanted to capture it all, but they started treating me like paparazzi—"Please, Mom, stop already!" Then I read a book about staying in the moment, and I stopped. Because if you put a lens here [motions to her eye], there's somehow a distancing, right?
Oprah: Yes. And in the Kodak moments, most people are taking pictures of the life they wish they were actually living.
Rosie: But you know what's interesting? Kelli came from a very debutante ball kind of family. It was like a life out of Dallas. All the photos in her house were of her family in the same outfits at the beach—which, to me, looked fake. But when I'd send pictures of the kids to Kelli's mother, she'd say to Kelli, "Why does she take the pictures when they have chocolate on their faces?"
Oprah: Because you like the chaos.
Rosie: That's when I'm like, "Click!" There was a time when I wanted the porcelain veneer. But as I grew up, I realized, wow, the beauty is in the cracks.
Oprah: And once you start looking, you realize the cracks are everywhere.
Rosie: Like with my mother dying. I was so hung up for so long on the story of that loss that I never took the time to realize how well she must have mothered me in order for me to have the desire and ability to mother the way I do. That had to come from somewhere. And now I actually feel a little lost because I never got to watch her mothering teens.
Oprah: The teen years have thrown you.
Rosie: Not so much with my son Parker. I'm madly in love with him. I would die for any of my children, and, more importantly, I would live for any of them. But there's something about Parker. When I look at him, I realize that my whole life is B.P. or A.P.—before him or after. Because he was the first. Because when you go from being a nonparent to being a parent, your entire paradigm shifts. So as much as my mother's death was a dividing line in my life—March 17, 1973—May 25, 1995, is when the lights came back on. Color entered the picture again.
Oprah: You and Kelli married in 2004 and divorced in 2008. I read that your split was one of the most difficult things you've ever had to deal with.
Rosie: Humbling. And humiliating.
Oprah: Because it felt like you failed?
Rosie: In the O'Donnell family, no one had ever been divorced. At 33 I adopted Parker. Then I adopted Chelsea. Then I met Kelli. And the plan was that you stay together forever. But when I left my show and when Vivi was born—three of the children are adopted, and Kelli gave birth to Vivi—everything shifted. I was no longer on TV. I had a lot of time. I was at home, trying to come down from the rarefied air at the top of the mountain and regain some kind of authenticity.
Oprah: At sea level.
Rosie: Yeah. And it wasn't clicking for either of us. We didn't like the same stuff. I would be in the pool every day with the children. And when we were in Miami, where I also have a home, I'd go out on my boat—I could spend ten hours a day on my boat, looking for dolphins. But Kelli didn't really like the boat or the pool. She plays tennis.
Oprah: And you hadn't noticed these differences when you were doing the show?
Rosie: I didn't have a lot of time. I was working, working, working. Then when we'd have a week hiatus, I was like, "Come on, we're all going down to Miami!" If Kelli was out shopping, it didn't matter—I'd just go with the kids. But later, when the separate interests became day after day, I found myself lonely—as she did, too. She wanted to play tennis at the country club, and I don't do country clubs. I tried. They made an exception for a gay family, and we joined. It was a big thing: "They let in a gay family—whoo!" So I show up to play with her, and somebody comes out and says, "You can't play unless you have tennis whites." I said, "Excuse me? I have to get dressed to come and play tennis at a club that I pay ownership fees to?" That was the last time I went. It's a different culture. I just didn't fit.
Next: Rosie discusses hormones, coming out, and reaching a new place in her journey