Olivia Wilde Opens Up About Age-Gap Romances & Earning Confidence

0:05This is The Run Through. I'm Chloe Mal. And I'm Choma Nardi. 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 everything I want it to be? Oh, my gosh. Choma, you're going to have so much fun. It is such a hoot. 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 and 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 And each one of them so sort of unexpected and funny and great in these roles.

0:59I 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 am not going to ruin anything about what happens when these two couples have their dinner party.

1:50But, 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.

2:28I 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 think of it as your Instagram handle. I know, I know. Wait, you have a blog, Choma? Let's unearth those. Oh, my gosh. You know, Sally Singer asked me to do it before I got the job, I think, as like a kind of like, you know, show us what you're made of kind of thing. Soft test. Soft test. So it's taking. So now I'm tasked with making content and I and I love the sort of loose personal aspect of yours.

3:04And I thought, damn, I've got to go out into the world and make some content. So that's what I did this week. Yay. What content did you make, Sharma? What did you see? So last night I swung by the Coco Goffs event. She's in town from Wimbledon and has also collaborated with Mimia Nubalis on this really adorable collection of tennis gear and sneakers. Spoiler alert, she will be wearing some of this on the court. And we chatted very briefly. She was inundated with fans and it was quite hard to get her attention. But when I did, she was absolutely delightful and I'm obsessed with her. So that was fun.

3:39Wait, are you going to Wimbledon? I am we're doing an event oh right we're doing an event with Ralph Lauren and Anna's going to be co-hosting and and my colleague Adam who is now the head of edit head global head of editorial content for GQ is coming over too so it's going to be big GQ um Vogue collab and so it'll be really fun the guest list is shaping up really nicely I can't tell you's on it but they're fab so lots happening lots lots happening and then last night was also the serpentine a garden party ran into a lot of great people both new yorkers i mean can you believe i was introduced to like mike bloomberg was there and lauren santo domingo flew over from she'd come in from paris i guess it's really hot in paris like 101 or something yeah and i saw wes gordon for breakfast which was nice and he was he was lovely and we were talking about our mutual love of you and he brought Olympia as his date to the party but who are your best dressed I don't know if you had a look but everybody here is talking about the fact that Sienna Miller who always looked flawless really committed to the Connor Ives look and wore this sort of fur trimmed in 95 degree weather I mean bless her heart she looked amazing she's obviously always a fave and then I thought Alexa Chung looked particularly great in this Dallara look which she came with Dallara Michael B Jordan was there which was like big deal for us to have such big celebs in the house um can you believe it was my first time that just tells you how late I am to the garden party what did you wear Choma so I wore a piece I got from the eBay sale actually I wore this Dries dress from a collection that was all floral prints and then these Dries pants.

5:24So basically like a slip dress over pajama pants. It's very floral explosion. So I'll send you a picky. So you'll see. I want to see. It was fun. What else do we want to talk about? Yeah, I do feel for everyone who's in Paris for Men's Fashion Week because it is just unprecedented heat there. I couldn't believe that Connor Story wore latex knee-high socks to the YSL show. I mean, that is just a level of sweaty sliminess I never want to endure. I also felt like it was such a sign of the shift in seasons that the cute Dior ushers went from their gray-knit polo sweaters to just pique polo shirts.

6:10And also, we've been talking about how everyone, the accessory of the season in Paris right now is the handheld fan. Charlie XCX currently had two, an electric one and a regular paper one. I feel like there's like a generational divide. The young guys have the electric ones and like millennials have the fan and maybe Charlie's somewhere in between. And I'd love to talk a little bit about the Vogue summer issue. I saw that there was an ice cream launch. I was very jealous and I want to know every flavor that was available on the menu. Well, there's one flavor, which is the Vogue flavor, Vogue a la mode.

6:47And it was a big team workshopping which we discovered that many Vogue staffers favorite ice cream flavor is mint chip. And we all felt like... Oh, weird. I hate mint. Mint. We were so surprised because it's my favorite but I was surprised that it was so popular and we really felt like the metublasification of fashion has made mint such a big fashion color right now. So we were like, let's do something with mint And I originally wanted to do mint espresso and do like chocolate covered espresso beans into your mint chip. I love that. I would be picking out those beans. We tried it and when they were cold, they were too crunchy.

7:27So we had to do different options and we worked with Morgensterns and Mr. Morgenstern helped perfect the flavor and made everything himself. and we ended up doing espresso-soaked honeycomb covered with chocolate, crushed up, and the crunch was delicious. I love honeycomb. Okay, maybe I can reconsider the mint. I think you should reconsider. You like mint tea. I do love mint tea. This is a fresh Vietnamese mint. How long is this going to be on the menu? When am I going to be able to? Two weeks. 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.

8:05Next door, we had a pop-up where we had all the photos from our World Cup U.S. 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 Ribbington Street. How cool. 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 that the CFDA United Flags of Fashion story for the anniversary, the big 250.

8:41I know. Tell me everything. How was that? It's been really a labor of love for Naomi Eliza, 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 Bodie did Georgia. And then other people just chose random states that they wanted to reinterpret.

9:19And it's been really fun to see what people have done with those designs. And for the summer issue, our 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.

9:59And this year feels like American summer. And that I think is the Knicks winning has been this 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 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.

10:38And 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-fifre-fiving each other in the street. And there's a real vibe and atmosphere. It's crazy. 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 Gardner party, I rushed home to see England versus Ghana.

11:11It was a draw. It's wonderful to see because there's so many, obviously, the players on the Ghana team that play for British teams and many British players who have Ghanaian heritage. So there's a real, it was really fun. It was a really intense match. I wanted both sides. I felt for both sides. But I have high hopes for the England team. Let's see. But I want them both to qualify. I want Ghana, because I've been basically rooting for all the African teams, like Cape Verde, Ivory Coast. Like there's amazing goalkeepers that have come through. I've been really, suddenly I'm just like all about it.

11:45We love the Congo teams, the designer of all their outfits. We interviewed the designer. I saw that. And he was fantastic. And it did really well. People were very interested in it. I definitely think they were the best dressed, like, arriving at the airport. And their fans were just a delight to see, too, all dressed up and with the drumming. I've been really into the football. And America have been doing so well, too. The USA have been killing it. It's been great. I know. And here I was saying that they were going to be crushed, but I think not. I'll take it back. Chalba, I hope you see Toy Story 5.

12:23It 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. Mumdani's endorsed candidates really came through. Another reason to be cheerful about New York, he seems to be like crushing it. It's true.

12:59The Run Through will be back in just a moment with Olivia Wilde.

13:11I'm Jazzy Seppcek. And I'm Shilpa Oskokovic. And we're senior test kitchen editors at Bon Appetit and the hosts of the Bon Appetit Bake Club podcast. Bake Club is Bon Appetit's community of confident, curious bakers. We love to bake. Some might even call the two of us obsessive. And we love to talk about all the hows and whys and what didn't work that come with it. Every month we publish a recipe on bonappetit.com that introduces a baking concept we think you should know. Then you'll go bake, send us any questions you have. And we'll get together here on the podcast to talk about the recipe. And this month, we are making whole lemon bars.

13:47Imagine lemon bars, but with just kind of the lemoness dialed up to kind of like a reckless decibel level. Head to BA.com and come and bake along with us. Send us your questions, pictures, and any thoughts to BakeClub at BonAppetit.com or find us on Substack. Join us the first Tuesday of every month as we debrief about our latest bake. Find BA Bake Club wherever you get your podcasts. Happy baking.

14:23I 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. I have to say, I was very, I was listening to a few podcasts you've done from before Booksmart and sort of a while ago.

15:04And I was very inspired by your very passionate plea to mothers to defy the guilt machine. Yes. And also very inspired by your moms traveling for three weeks in war zones in a time when there was just a scratchy phone line. I mean, now I feel like there is this like tyranny of FaceTime because you feel like you have to FaceTime all the time and they don't really want to. They don't really want to. That's what I have found. My kids are like, they feel kind of like bullied into it by me. They're like, hi. And I'm like, and what happened then? They're like, listen, can we just talk about this in person later?

15:38And I'm like, okay. And also you were saying this was obviously, when was Booksmart? Five years ago? Six years ago? Yeah, something like that. You were saying that you were talking about whether to start sort of integrating your kids more into your work life. Right. And that's something I've been thinking about because my kids are four and six and they love coming to visit here. And actually, my son listens to Goosebumps with like on podcast. It's like a mom and her son reading. He's like, we should do a Goosebumps podcast. And I was like, I should bring him in here. I think creating projects with them is the best idea because then they equate you working as some kind of sign of the work ethic you'll put into a project with them.

16:16Like my son and I made a little children's book together that was a combination of recipes and silly stories. And it was the most fun thing we ever did. And I think that the problem is I keep making movies that are rated R that they just cannot possibly come to set. But although on the invite, I was in the sound mix at one point and my son came to visit and I thought it would be cool because we were at Abbey Road and he's a musician. And I was like, yeah, come to Abbey Road. And he sat in and watched these scenes that I realized only then were the most inappropriate scenes to be showing a child.

16:47And I was like, I have failed in several ways now. I have traumatized him. It's literally me talking about like pegging. It's not okay. And I'm like, this child has seen too much. So I'm still working it out. How much are they curious about what you do? Curious? And they're very supportive and they feel a sense of responsibility. A sense of like that they are sort of my agents and representatives. Like they will say, what do you have on the table? What are you choosing between? And I'm like, well, I want to do this movie. They're like, don't do that. That's too similar to this other thing. And there's.

17:22No, 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. Like, I remember when the first billboard for the A24 film, Backrooms, 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 make it something like do that, find that kind of thing. And I was like, God, I should just listen to them more. Wow. I now I'm putting together a Christmas comedy and I pitched the entire thing to my daughter who's nine the other day.

18:04And 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? Sports are big. 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.

18:41And 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. 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.

19:20Oh, my God. So she could hear them talking. And I just was amazed. Did she watch F1 in life? No, she just understood it to be what she was seeing in real life in that moment, kind of understood the concept. And I was like, listen, this is the most extreme version of this. Like, this is Monaco. This is not, you know, if you're going to start anywhere with F1, like, it really doesn't get more exciting than this. Yeah. And she was locked in. And I just was, I'm continuously amazed by them, But I just was so kind of proud of her for just taking an interest and being really curious and being so game.

19:57It was very fun. And you guys wore matching dresses. We did. Which was kind of an accident. I was like, we're not these people. And she even said, she goes, oh, mommy, oh, no. This looks like we did it on purpose. And I was like, it's fine. Is she interested in what she wears and what you wear? She is. And she now is wearing a lot of my clothes. Really? At nine? She's very tall. So everyone else in my family is very tall. I'm the only person under six foot. And she's going to be like my sister, who's almost 6 '2". And she's nine and a half, but her legs are probably longer than mine at this point.

20:33And she wears everything. She wears my shoes. We have the same shoe size. Not for long. She'll grow out of them. But it's really interesting because it's created this whole other bond with us. And I'd say she's a lot more stylish than I am. She's a lot more thoughtful. Does she go to a school with a uniform? No. She did for a while. In London, for a bit, she did. And I felt like it robbed her of a level of self-expression that I think she takes great pride in. And I love seeing the choices she makes. I also have to, like, hold back from any criticism that we realize, like, God, the way that seeps in and your mother thinks it's advice, but you internalize it deeply.

21:12And I was, so I just kind of, I'm like, yes, I love how many freckles you've drawn on. It's much better than what I was doing. I was going through like the entire manic panic hair care line and like putting like complete toxic shit in my hair and dyeing it like mud green. And my poor mother was just like, why? So she's better. Did you dye your hair for? I want your sex. I want your sex. That is a wig. Okay. I was wondering that. That is a wig. But ironically, I wore a wig for that and then immediately dyed my hair for another thing. and I was like, I really could have avoided the wig. But that was a wig that was inspired by a few different people, but I had this image that it was sort of a combination of like Bridget Bardot and Barbarella and like Nadia Lee Cohen.

21:56It was very Nadia Lee Cohen. It was very Nadia. And it was so fun. I have not seen I Want Your Sex yet, but I'm very excited about it because I want to talk about the invite after. But while we're talking about I Want Your Sex, I want to know how that came to be. And you play this sort of unhinged artist dominatrix. Have you ever played something like that before? No. That was also Greg Araki is a real auteur and an icon of 90s queer cinema and really a singular filmmaker. He has an approach that is very unique and a style and a kind of irreverence that I've always been really attracted to. And he approached me with this character, and I loved the kind of no-holds-barred, truly-not-giving-a-fuck energy of this woman.

22:51And I understood that Greg had really created this character as a way to kind of express a lot of his own opinions about sex today, Gen Z's opinions and practices with sex. And he just had this kind of ethos about the whole thing that was so liberating. And I very much wanted to kind of crawl inside his imagination and just serve his project. And this character was, I mean, such a badass. I really, I took a lot from Madonna, specifically rewatching Truth or Dare, which I think has to be one of the greatest music documentaries. I just tried to tap into the part of her that is so confident from a very real, authentic place.

23:40And so I tried to muster that in this character. But it was just so fun. It looked from the trailer like it was so much fun. And it kind of reminded me of your character on The O.C., which I feel like is where a lot of us first were introduced to. You're not wrong. There is a real crossover there. I think that character was like the teenage version of this woman. The same kind of very independent spirit. The funny thing is, in The Invite, I play a woman who's like riddled with anxiety and insecurity. And so the two are clearly the two sides of my personality. I exist somewhere swinging wildly in between these two sides.

24:18But I Want Your Sex was like, put on the most incredibly designed latex outfits, all designed by Ariane Phillips, who's the most incredible costume designer. And then put on this incredible wig and just be this person who is living completely by her own terms. Who has a sort of May December romance with Cooper Hoffman, who I just think is. Well, yes. That's what I was about to say is that he is, I think, the most exciting young actor working today. There's a different, I think, much more interesting process of establishing oneself as an actor today. And I think Cooper has done this not only in the shadow of his brilliant late father, but also just in this industry where there is a kind of homogenization of actors.

25:02He has continued to just be his own person. Yeah. And he's so good. I mean, and I do feel like there's such an interest right now. We were just talking about it. yesterday with some colleagues in these stories about May-December romances. There's the Natalie Portman movie coming out, which people are so excited about. What do you ascribe people's fascination with that to? I think that art in all forms has for centuries explored fantasy and the forbidden. And I think that particularly older women, younger men is still such a taboo in this culture, that it's through art, it's through literature and film that we really kind of allow ourselves to play.

25:50It's interesting because it's between Baby Girl and there's been so many films in the last couple of years, and ours is definitely a camp extreme version of it. But I do think that people are starting to, I think, like get a little bit more French about it. You know what I mean? I hope so. Just like relax. Yeah. I was going to ask you if you have any personal experiences you were drawing from, but then I got nervous about asking. I love your honesty about that. I was like, yeah, sure. But everyone is going to ask you that. Everyone will ask me that. It's not, it's true. I think that experiencing the double standard firsthand has been fascinating from a sort of anthropological standpoint, if one can, like, remove oneself from one's body and look at and zoom out.

26:36And it is so much more egregious than I think I ever really thought. Interesting. You get the sense, like, hey, it's 2026. People have come a long way. People won't have such a double standard about what we allow women to do in this world when it comes to romance, not to mention their careers and motherhood and all these other things that we traditionally sort of enjoy seeing men do in any way they want. The double standard, not only when it comes to beauty, but in terms of, like, life choices. I knew that was a thing that was real, just like we're aware of, like, pay discrepancy. We're aware of these things.