The Run-Through with Vogue
Olivia Wilde Comes Clean: Age Gap Romances & Earning Confidence
25 Jun 2026
Transcript generated automatically by AI and may contain errors.
Chapter 1: What is the main topic discussed in this episode?
This is The Run Through. I'm Chloe Mao. And I'm Cho Minardi. And on today's episode, we are bringing you a conversation that I had last week with director and actress Olivia Wilde.
Oh, my God. I cannot wait to see the invite. Is it is it everything I want it to be?
Oh, my gosh, Choma, you're going to have so much fun. It is such a hoot.
Chapter 2: How do Olivia Wilde's children influence her work?
I have to say the first 30 minutes I was like, hmm, I'm not sure if this is for me. And then I got so into it and just it I was laughing out loud. It's really like a chamber drama in itself. It could be done on the stage. It's in one location, which is why they filmed it in chronological order. And it's really these four characters interacting as a quartet for the entire film.
And they are all so fantastic. It's Olivia Wilde, Seth Rogen, Penelope Cruz and Ed Norton. And each one of them so sort of unexpected and funny and great in these roles. I really enjoyed it. This is Olivia's third film that she's directing, and it's coming to theaters on Friday the 26th, this Friday.
I got to see it early with some colleagues, which, no spoiler alert, but it can be an awkward movie to see with your colleagues.
Okay. Noted.
Including Anna. Okay. And it's a remake of the Spanish film The People Upstairs, which is also known as Sentimental. And it's about two couples and it sort of felt like a zany 2026 version of Who's Afraid of Virginia Woolf, but sort of gone awry, even more awry. And I'm not going to ruin anything about what happens when these two couples have their dinner party.
you know, maybe something, you know, you didn't anticipate with your neighbors. But we also talked about Olivia's role as artist and dominatrix in Gregor Rocky's new movie, I Want Your Sex. And the subject matter of that film brought us to the double standards of being a middle-aged woman dating a younger man, which is something we know Olivia has had some experience with.
So I was a little nervous to ask her about that, but she was very frank and wise about it. So I'm excited for you to, you know, tune in. Choma, what is happening in London? Tell me about your newsletter, and I'm obsessed with you calling it Naughty by Nature.
I thought malware was pretty freaking brilliant, so I dug deep and I went back to an old moniker of mine, Beloved, that was on Instagram. In fact, I think I used to have a blog that was called Naughty by Nature.
I mean, I think of it as your Instagram handle.
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Chapter 3: What insights does Olivia share about her role in 'I Want Your Sex'?
When am I going to be able to? How long is this? I'm going to have to save a pint for you. Save a pint for me. Oh my God, please.
But it was really fun because we made it like a little block party. Next door we had a pop-up where we had all the photos from our World Cup U.S.
Chapter 4: What challenges does Olivia face as a middle-aged woman in the film industry?
men's national team shoot with Iman, which I loved. And then next door to that was Iconic Magazines, which had Gracie Abrams' issue, the summer issue, in the cover and wrapping around. And so it felt like this fun takeover of Rivington Street. And it was really fun. It was exciting.
And for anyone who came the first 200 scoops of ice cream, if you subscribed to Vogue on the spot, you got a free scoop.
I love that. I love that. I also saw the CFDA United Flags of Fashion story for the anniversary, the big 250. Yeah.
Chapter 5: How does Olivia describe the dynamics of May-December romances?
I know. Tell me everything. How was that? It's been really a labor of love for Naomi Elize, who's been working on this with some other members of our fashion team, with the CFDA. And basically, it was a way to reclaim the American flag, which feels like in the last few years has gone very sort of MAGA and weighted politically.
CFDA asked over 100 American designers to design their own version of a state flag. And so certain people designed flags that meant something to them, like Michael Kors did New York and Bode did Georgia. And then other people just changed. chose random states that they wanted to reinterpret. And it's been really fun to see what people have done with those designs.
And for the summer issue, art designer Hazel did an amazing sort of patchwork quilt of all the flags, and we photographed it. In backdrops of American state parks. And so that was really fun. And it looks really beautiful. And then they're going to fly all the flags at Rockefeller Center at the end of July. So there's going to be a flag raising event, which I think will be really fun.
There is like a situation on TikTok right now and beyond where grass is greener in terms of people's Instagram adventures in Europe. And it's like Euro summer. And this year feels like American summer. And that I think is the Knicks winning has been an amazing moment in New York. And the World Cup being in the U.S.
and Mexico and Canada has felt like this amazing sort of summer of sport in the U.S. And it just feels very exciting. Like people are sort of appreciating their hometowns a bit more than wanting to go further afield. Also, it's so expensive to fly transatlantically right now because of oil prices that I think people are trying to look closer to home. And Nicole Phelps has a great website.
article that goes live today on national parks and visiting national parks and the best way to do your national park tourism, which I've never done. And I'm really now inspired.
That's definitely on my bucket list. I keep getting messages from friends in New York saying it's like it feels like the best summer in New York ever. Exactly. People are high fear five over each other in the street. It's so there's a real vibe and atmosphere.
It's crazy. Cool. It's really amazing. Choma, have you been watching the World Cup?
Yes, I have been glued to the screen because my dad is in town and all that he wants to do is watch soccer, obviously. Thankfully, there's a five-hour time difference because after the Serpentine Garda party, I rushed home to see England versus Ghana. It was a draw.
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Chapter 6: What unique storytelling approach did Olivia take for 'The Invite'?
I know, and here I was saying that they were going to be crushed, but I think not. I'll take it back.
Chalda, I hope you see Toy Story 5. It is so good. I cried. Okay. And then I went from Toy Story on Saturday to Film Forum, which was playing a third man, which is one of my very favorite movies, and I'd never seen it on a big screen, so that was really fun. There's a Carol Reed... retrospective at Film Forum right now. So I was delighted to see that. And we had New York's primaries on Tuesday.
I voted before work. Mamdani's endorsed candidates really came through.
Another reason to be cheerful about New York. He seems to be like crushing it. It's true.
The Run-Through will be back in just a moment with Olivia Wilde.
Hi, this is Bella Freud. Each week on Fashion Neurosis, I interview highly creative people in the world of fashion, film, art, sport, literature, and music. The format of the show is that my guest lies on the couch and I sit in a chair like an analyst. I know.
I ask questions, quite simple things that revolve around how we reveal or hide things through what we wear, how we do or don't draw attention to ourselves. Find Fashion Neurosis on YouTube or wherever you get your podcasts.
I am so excited, Olivia, to be here with you today. Thank you so much for coming in. This is such a treat for us. Thank you. Thanks for having me. I want to know, what's your summer schedule? Like, what is today coming from?
I am in the midst of this kind of final push for our film. Okay. And so I run in between screenings. Okay. Luckily, it's for a movie that I love, so it's joyful, but it is a constant thing. I'm also prepping another movie and attempting to not, like, fail as a mother and friend. So, you know.
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Chapter 7: What reflections does Olivia have on beauty standards and aging in Hollywood?
They're like, don't do that. That's too similar to this other thing. No, really? How old are they? They're 12 and 9. Okay. And they really feel like they have a strong handle on, like, the marketplace. It's really funny. Wow. I remember when the first billboard for the A24 film, Back Rooms. Yeah. appeared, and I didn't know what it was because I'm not plugged into the YouTube community.
And my son was like, that will be huge. Wow. And he said, that will be huge. You should do a movie like that. You have to find something like that and do that, find that kind of thing. And I was like, God. I should just listen to them more. Wow. I'm putting together a Christmas comedy, and I pitched the entire thing to my daughter, who's nine, the other day.
And actually, she picked out two things that we hadn't thought through that were so clever. And I thought the act of kind of pitching these things to them not only actually helps me because they're smart, but also it allows them to feel like my work isn't this separate thing that they are kind of abandoned for.
I saw that you and your daughter just went to the Monaco Grand Prix. We did. Was that... Are sports big in your household?
Were you excited about the Knicks? Very excited. Are you excited about the World Cup? Very. The Knicks were... That was a major thing for us. We are lifelong Knicks fans, and the kids love going to Knicks games, and that was a big, big deal. And the Grand Prix was a new thing for Daisy. She's never really watched F1.
So I was curious, as one is when you bring your kid and you think, are they going to be really bored? Are they going to be nagging me the whole time to leave? And I was prepared for that. And I thought maybe she'd think it was too loud. It's so overwhelming. It's so crowded.
Yeah.
This little woman puts on the headset for two hours. She did not speak to me. I'd be like, do you want water? And she'd be like, shush, shush, shush. She'd be like, I can't. Just stop. George is having trouble. And I'm like, this is incredible. And the very kind Mercedes team engineers put her on their, like, radio. Oh, my God.
So fun.
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