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

The Run-Through with Vogue - Vogue

Olivia Wilde discusses her new film, directing challenges, motherhood, and societal pressures on women in Hollywood. The conversation spans creativity, aging, and authenticity in the entertainment industry.

Key takeaways

• Directing her third film is both joyful and demanding
• Motherhood and work-life balance remain complex
• Age-gap relationships face societal scrutiny

Transcript preview

This is the run through I'm Chloe Mal and I'm Chamonardi and on today's episode we are bringing you a conversation that I had last week with director and actress Olivia Wild 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 gonna 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 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 Wild Seth Roggen, 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 is sentimental and it's about two couples and it sort of felt like a zainy 2026 version of who's afraid of Virginia Wolf 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 but you know maybe maybe something you didn't anticipate with your neighbors. But we also talked about Olivia's role as artist and Dominatrix and 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 my brilliant so I dug deep and I went back to an old moniker of mine beloved that was on Instagram and I think I used to have a blog that was called Nardi Bo Lature that was I think of it as your Instagram handle I know I know I know. Wait you had a blog choma let's unearth those oh my gosh you know Sally Singer asking me to do it before I got the job I think has like a kind of like you know show us what you're made of kind of thing I had soft test so it's and I love the sort of loose personal aspect of yours and I thought I'm damn I've got to go out into the world and make some content so that's what I did this week yeah what what content did you make chama what did you see so last night I swung by the cocoa goths event she's in town for Wimbledon and as also collaborated with miumi on this really adorable collection of tennis gear and sneakers spoiler alert she will be wearing some of 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 that was... Are you going to Wimbledon? I am we're doing an event we're doing an event with Ralph Lauren and Anna's gonna be co-hosting and my colleague Adam who is now the head of edit, head of editorial content for GQ is coming over to so it's gonna be big GQ QQ co-lab and so it'll be Solicis is shaping up really nicely. I can't tell you is on it, but they're fab. So lots happening, lots, lots happening. And then last night was also the Serpentine 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 Paris, 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 breakfast, which was nice, which was nice, which was nice, which was nice, which was nice, which was nice, which was nice, which was nice, which was nice, which was nice, which was nice, which was nice, which was nice, which was nice, 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 stress I don't know if you had a look but everybody here is talking about the fact that Siena Miller who always looked flawless really committed to the Connor I've's look and wore this sort of fur trimmed embroidered 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 Delara look She came with Delara. Michael B Jordan was there, which was like big deal for us to have such big celebs in the house. Wow. Can you believe it was my first time? That just tells you how they am to the garden party. What did you wear, Choma? So I wore a piece that I got from the eBay sale, actually. I wore this drees dress from a collection that was all floral prints and then these drees pants. So basically like a slip dress over pajama pants. It's very floral explosion. I'll send you a picky. So you'll see. I want to see. It was fun. What else 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 Yousel 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 shiminess. in seasons that the cute Dior ushers went from their gray-knit polo sweaters to just PK polo shirts. And also we've been talking about how everyone the accessory of the season in Paris right now is the handheld fan. Charlie XeX currently had two an electric one and a regular paper one. I feel like there's like a generation of divide. The young guys have the electric ones and like millennials have the fan and maybe maybe Charlie somewhere in between. And I'd love to talk a little bit about the the vogue summit 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 alamode and it was a big team work shopping which we discovered that many vogue staffers favorite ice cream flavors mint chip and we all felt like... I hate. favorite but I was surprised that it was so popular and we really felt like the metublazification 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 but I love that I would be picking out those beans. We tried it and when they were cold they were too crunchy so we had to do different options. and we worked with Morgan Stearns and Mr Morgan Stearn helped perfect the flavor and made everything himself and we ended up doing espresso soaked honeycomb. I do love minty I do love minty. This is a this is a fresh Vietnamese mint. How long is this going to be on the menu? Okay maybe I can reconsider the mint. I think you should reconsider. You like mint. I do love minty. This is a fresh Vietnamese mint. How long is this going to be on the menu? I know why it save a point 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 US men's national team shoot with im on 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 take over of Rivington street and it was really fun it was exciting and for anyone and for anyone who if you subscribe to Vogue on the spot you got a free scoop. I love that I also saw that the CFDA United Flags of fashion story for the the anniversary the big 250 I know tell me everything I 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 waited politically, CFTA asked over a hundred American designers to design their own version of a state flag. And so certain people design flags that meant something to them, like Michael Coors did New York, and Bode did Georgia, and then other people just 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, Hazelle, 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 gonna fly all the flags at Rockefeller Center at the end of July so there's gonna be a flag raising event which I think will be really fun. There is like a situation on Tik-Tococococ right now and beyond where grass is greener in terms of people's Instagram adventurers 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 this amazing moment in New York and the World Cup being in the US and Mexico and Canada has felt like this amazing sort of summer of sport in the US and it just feels very exciting like people are sort of appreciating their hometowns a bit more than wanting to go further a field also it's so expensive to fly transatlanticly right now because of oil prices that I think people are trying to look closer to home and Nicole Phelps has a great article 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 then there's a real vibe and atmosphere. It's crazy. It's really amazing. 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 Garden Party I rushed home to see England versus Ghana. It was a draw. It's wonderful to see because there's so many obviously players on the Ghana team that play for British teams and many British players who have Ghana in 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. I've 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 we love the Congo teams the designer of all their outfits we interviewed the designer so that he was fantastic and it did really well people were very interested in it I definitely think they were the best they were the best dressed at the airport. Like and their fans were just a delight to see too all dressed up and with the drumming and yeah I've been really into the football and America have been doing so well too the USA have been killing it. I know it's been great I know and here I was saying that they were gonna be crushed but I think not I'll take it back. 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 a retrospective at film form right now so I was delighted to see that and we had New York's primaries on Tuesday I voted before work mumb donnie's endorsed candidates really came through another reason to be cheerful about New York he seems to be like crushing it's true The run through will be back in just a moment with Olivia Wild. This week on critics at large, we're talking about