Ali Wentworth Gets Complicated (2023)

She’s starring opposite Meryl Streep in It’s Complicated. Her husband is GMA’s new host. The Oprah regular tells Kevin Sessums about talking dirty with Alan Greenspan.

“I come from a very la-ti-da East Coast intellectual family—or so they think,” says Alexandra Wentworth, pouring a bit of cream into her Earl Grey tea. “And there I was in L.A., measuring my self-worth by whether I could book a job on Beverly Hills 90210.”

Ancient history. It’s been a big year for both Wentworth and her husband, George Stephanopoulos, who recently left ABC’s premiere Sunday-morning political show, This Week, to take over for Diane Sawyer on the network’s morning program. “ GMA is a completely different animal than This Week,” she says. “And George does have that side. He’s incredibly warm and funny and engaging, but he just has never had to use that muscle in his job before.”

“She said, well, I could set you up with my ex-boyfriend, George Stephanopoulos. And I said, no, not interested. I said set me up with Matthew Perry or Hugh Grant, but not anyone from politics.”

Wentworth, for her part, has appeared in Jerry Maguire, played Jerry Seinfeld’s girlfriend in the “Soup Nazi” episode, created and starred in the cult hit Head Case, and lately has been appearing on Oprah as a special correspondent. Now she’s rounding out the year playing Meryl Streep's character's best friend, along with Mary Kay Place and Rita Wilson, in the sure-to-be-blockbuster romantic comedy, It’s Complicated.

Except for her parents’ divorce when she was a year old, Wentworth has, in fact, led a rather charmed life. Her mother, Mabel “Muffie” Cabot is a Washington and Boston society doyenne whose own mother, Janet Elliott Wulsin, became a pioneering explorer, leading expeditions to China, Tibet, and Outer Mongolia in the 1920s. Muffie Cabot served as Nancy Reagan’s social secretary, and Wentworth’s father was a reporter for The Washington Post. “I spent a lot of time during my childhood at the offices of the Post,” says Wentworth. “I loved playing in those offices as a girl.”

After we finish our tea, she’s taking her own girls, 7-year-old Elliott and 4-year-old Harper, to dinner at their paternal grandparents’ apartment here in New York—grandfather Robert Stephanopoulos, the dean of Holy Trinity Greek Orthodox Church, and his wife, Nikki. “It’s all about Elliott and Harper later. I could show up naked and Robert and Nikki wouldn’t even notice.”

You’re moving to New York from D.C. Weren’t you part of A-list Washington as a kid? You used to do comedy skits for Nixon and Kissinger in your mother’s living room when you were 5. Anybody who could make those two laugh was destined for a career in show business.

But at 5 years old, I wasn’t aware of how A-list it was. Just like Tori Spelling didn’t know she was on Farrah Fawcett’s lap growing up. No, I take that back, she probably did. Yeah, I grew up in that world of power and politics in Washington, but when you grow up around it, you are completely unfazed by it. Still am. George and I had our first real dinner party during the Obama inauguration because during the Bush years no one went out after eight. But most of the time in Washington I was pregnant and having kids. We could have been living in Guam.

Were you raised to be a Republican or a Democrat?

A Democrat. My mother was the only Democrat in the Reagan White House.

Who was the first first lady that you remember meeting?

That would be Jackie Kennedy. She was a good friend of my mom’s…. I met Lady Bird. Rosalyn Carter once gave me a big kiss on the cheek that was on the cover of The Boston Globe because she was attending an exhibit that my mother had curated during the Bicentennial all about the first ladies. Betty Ford kissed me, too.

Was she tipsy at the time?

No, she was sober. But who could tell, especially with women her age. I know with a lot of older women who haven’t had a drop to drink that I’ve often thought they were drunk.

How about the two Bushes? Sounds like a burlesque act.

Barbara Bush seemed fine. Didn’t spend a lot of time with her. But Laura Bush was so good at putting on a smile and saying everything is great and how good it is to meet you. All that Southern hospitality stuff. Then I found out she was a chain smoker and I loved her. When I first moved to D.C. with George, I was still a smoker and I actually met a lot of my friends by going outside at dinner parties to have a cigarette with them, like the Kuwaiti ambassador’s wife who became a really good friend of mine, my first one really when I moved back to D.C. We met smoking cigarettes together. There’s an instant sort of intimacy between smokers when you’re freezing your ass off outside a black-tie party. I used to say to George that I felt bad when we’d go to those dinners in Washington and some big mucky-muck had to sit next to me. He or she didn’t care what I had to say about nuclear proliferation. I’d get seated next to Alan Greenspan a lot for some reason at those dinners. And you know what I found out? He just wants to hear a good dirty joke.

I understand it was one of your oldest friends, Holly Peterson, who set you up with George on a blind date.

Oh, so she says. That’s not true. She was a part of it. I’m going to tell you the real story. I’ve never told anybody this on or off the record. I was living in Los Angeles and I had just gotten out of a relationship with a British actor, Dominic West from The Wire. I decided to have a kind of girl party for my best friend who works at CAA, Michelle Kydd. There was another girl there who was also suddenly single so I told her I was going to set her up with my brother who was living in L.A. at the time. I told her he was great looking, offbeat, went to Brown, worked for David Lynch. So then everybody said to her, come on, you’ve got to set Ali up with somebody. This is how the dating world works. She said, well, I could set you up with my ex-boyfriend, George Stephanopoulos. And I said, no, not interested. I said set me up with Matthew Perry or Hugh Grant, but not anyone from politics. And she said, no, no, no, he’s really great, and if nothing else it will be a good dinner party story. And I said, OK, next time I’m in New York, maybe. So the next time I was in New York I was at Holly’s and, of course, Holly being a Greek socialite almost lost her mind. I mean, the first thing she said was, “I'm supposed to marry George Stephanopoulos!” So she concocted a dinner party that didn’t exist and called him up and said, “I understand you’re supposed to be set up with this good friend of mine,” and she started naming all these mutual friends of theirs that were going to be at the party but he was out of town and couldn’t make it. Not sure what would have happened if he’d said yes. Guess she would have had to round up some people.

Anyway, after that I called him myself and he said, “What about dinner?” And I said, “What about coffee?” And he said, “What about lunch?” So I told him to meet me at the restaurant at Barneys because I knew I could still get my Kiehl’s body scrub if the lunch was a complete disaster. I tell you, I had no expectations. I knew who he was. I thought we’d have a great talk about Clinton and the White House. I’d read his book. In fact, this is another aspect of all this that I find fascinating. When Dominic and I were ending our relationship—he was moving back to London and we knew logistically it just wasn’t going to work—we took one last trip to Hawaii together. And the whole time Dominic was reading All Too Human by George Stephanopoulos. So all my pictures of Dominic on that trip are of him lying on the beach reading that book. There are even pictures of him napping with the book opened across his face so that what you see is his body with George’s face in place of his. That whole weekend he kept trying to read to me from the book. “Listen to this bit about when he met Hillary,” he’d say. And I’d go, “Would you shut up? I don’t give a shit.”

So, anyway, I went to have that lunch with George expecting it to be a perfectly nice lunch, nothing else, and I am telling you, halfway through lunch I suddenly couldn’t eat. My pits were sweating. We were both just talking gibberish by that point. I had my hair up in a clip and I do remember making a point of taking that clip out. At the end of lunch, he shook my hand and said, it was very nice to meet you. And I thought, well, that’s it. Because in L.A. they try to bed you—doesn’t matter what time of day it is. But then he called me later that afternoon and Holly was standing behind me whispering to me to play hard to get, tell him you’re busy. He asked me what I was doing the next night and I said I wasn’t doing anything. In fact, I told him I wasn’t doing anything later that very same night either, but he said he actually had to work. We were engaged two months later. We’re now in our ninth year and still when he walks in a room I get a little shiver. The passion is all still there.

Who was he dating before he met you?

Manhattan.

I know you’ve stopped doing Head Case because it was making you a head case yourself.

Yeah. I came down with shingles I felt so much pressure flying back and forth to L.A. to do that show and still trying to be a wife and mother back in D.C. I just had to stop the madness.

Are you still going to be working with Oprah in 2010?

Yeah, I have a deal with her. I love Oprah to death. I’d marry Oprah if anything ever happened to George.

Would you consider sending your girls to your alma mater, the tony Dana Hall School for Girls in Massachusetts?

I would never send my kids to a single-sex school. I would prefer them not to have eating disorders and treat each other like boyfriends. It was like being in a women’s prison. I really was like, I’m going to turn into Martina Navratilova if someone doesn’t get me out of here.

But in It’s Complicated, you’re part of a kind of gaggle of girls that Meryl Streep’s character lets her hair down with. There is a kind of schoolgirlish quality to those scenes. Though I really wanted to eavesdrop on what went on between the takes with you and Rita and Mary Kay and Meryl.

We had the best time. I mean, how could I not have a good time getting to say to Meryl Streep, “I read online that a woman stopped having sex and her vagina closed up.” That was just fun to say. But you’re right. Between takes we’d hang out together instead of going off to our trailers. We’d talk about Bernie Madoff—Meryl was fascinated by him and wanted to dissect him—and we’d talk about this great recipe she’d just found for banana bread. Stuff like that.

When are you going to write a book about your own extraordinary life?

Funny you should say that. I just closed a book deal with HarperCollins to do a memoir.

So you’ll be sharing a publisher with Sarah Palin.

Yes. It will basically be the same book.

Kevin Sessums is the author of The New York Times bestseller Mississippi Sissy, a memoir of his childhood. He was executive editor of Andy Warhol's Interview magazine and a contributing editor of Vanity Fair and Allure. He is a contributing editor of Parade. His new memoir, I Left It on Mountain , will be published by St. Martin's Press.