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Elizabeth Day
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Lily Allen
Foreign.
Elizabeth Day
Welcome to how to Fail with me, Elizabeth Day. Today I'm diving back into the archive to bring you a curated selection of some of my favorite conversations, moments that are honest, hilarious and most importantly, deeply human. This episode is all about your 20s, that rollercoaster decade of discovery, chaos, heartbreak, joy and figuring out who you are, or at the very least, who you're not. Whether you're in the thick of it, about to enter it, or reflecting with it in your past. I hope these stories bring you either a little comfort or insight. Maybe they just bring you entertainment. That's fine too. First up, Phoebe Waller Bridge. She speaks candidly and hilariously about one night stands, disastrous dates, and why you couldn't pay her to relive that chapter of her life. It's messy, honest and full of the kind of wisdom that only Fleabag can offer. Then we hear from Lily Allen, whose 20s were far from ordinary. From releasing sheezas to battling postnatal depression, navigating a breakdown while on tour and facing the collapse of her marriage. It's raw, real and utterly compelling. Lily shares it with clarity and courage and I promise you'll be glad you listened. Let's get into it.
Interviewer/Host
Do you think you failed at relationships in your 20s?
Phoebe Waller-Bridge
Oh, yeah. Yes, gloriously. I mean, I think even when you first said to me this is a podcast about failure, I thought I could feel because you're such a positive person and I could already feel the glory of what you meant there. Like what's the glory in failure? And I think fighting so hard to be so in love with someone with all that passion in your 20s and teens and then throwing everything at it and then it not working or like there being so much pain. And that is the stuff that so much creativity comes out of. So out of those painful breakups or miscommunications or just those horrible sticky one night stands or whatever. It is something you grow in those moments and so I value them all.
Interviewer/Host
A sticky one night stand is the best expression ever. The next day's stickiness. As you get back into the knickers, can you think of the worst date you've ever been on? Or the worst one night stand?
Phoebe Waller-Bridge
Let me flick through my diary.
Interviewer/Host
Your Rolodex, your extensive Rolodex.
Phoebe Waller-Bridge
I wish I had a date diary and that actually would prove very useful. Now. The worst date I ever had. There's just the ones where you just don't click at all and you feel yourself just sort of falling slowly into a chasm of boring the other person to tears. I don't know. There was one when I. There was a guy, I'd. We had a couple of dates and then he'd stayed over and the next morning it was quite clear to me that like this wasn't going to go anywhere. And I think for him as well. But a song that I really love is James is At Last. I'm always singing it like it's just the earworm that I always have. And I remember I was walking, I was living in a flat that was really on like a fifth floor or something. I was walking down the stairs and I was walking in front of him as we were going to go for breakfast or whatever and I was singing at last all the way down the stairs and like my love has come along. And when we got to the bottom Stairs. He was like ashen faced and like shaking. And I was like, what? He was like, I didn't realise this had meant so much to you. I was like, oh, God, no. God, no, no. That was pretty dire. That led onto a very. An awkward breakfast. I mean, they all sort of feel gloriously muddy. See if I can think of another one as we go along.
Interviewer/Host
Are you glad that you don't have to live your 20s again?
Phoebe Waller-Bridge
Yes. Like there's a brilliant line in Girls and she goes, you couldn't pay me to be. One of the characters in the first series says, you couldn't pay me to be 20 again. And then I think Lena Johnson's character says, well, they don't pay me anything at all to be in my 20s. I love that line so much. Yeah, I feel like I did it, I committed to it. I'd really like to have the skin from my 20s, but I prefer my heart and my guts now.
Interviewer/Host
I mean, your skin's amazing. That sounds like such a creepy thing for me to say right now. But you're bathed in the evening sunlight of East London.
Phoebe Waller-Bridge
Do you remember when we got quite pissed one night and I was going, I used to have a porcelain fish forehead. Alabaster, alabaster, alabaster. But then even that kind of stuff, like women can be so haunted by or hunted by as they get older because we're taught to be hunted by it as we get older. There's so much humour in that and there's so much life in that kind of stuff. And it's the gloom of self loathing that was supposed to grow around us as we get older and start fearing that our value is diminishing has been the opposite experience for me actually. You know, as all that kind of stuff comes and you realize, actually, no, this is just. I feel like there's a message from society and billboards and all that kind of stuff that is teaching us to sort of hate ourselves. And I've always felt like that was a kind of way of controlling us. And the moment I realized that, I was like, oh, you're just trying to control me. And then that flicked my rebellious switch even more. And now I just feel way more fierce than I ever did in my 20s.
Interviewer/Host
When you say it's a question of control, do you think it's control that stems from men having been in charge?
Phoebe Waller-Bridge
Yeah, yeah, absolutely. I mean, I can't imagine that women en masse operating at that level would want to pedal the same message. So I think so, but I think it's something we've become so used to. I think that's the problem, that I don't think that it's every man in the world saying that this is an impossible standard that women should live up to. I think, actually, I mean, it's probably like, sinks in somewhere because it's something that we're so conscious of all the time as women, and probably on some level men are as well. But I feel like it's just the habit that we need to break. And I have faith that we will. As more women climb higher up that pole, dance, swing higher up that pole, as we do, we reclaim the pole.
Elizabeth Day
Do you feel because Fleabag has been.
Interviewer/Host
So totemic for so many women, particularly young women in their twenties?
Phoebe Waller-Bridge
Didn't this say poll, she said totem, It's a much classier way. I've been swinging my body around that totem as much as I possibly can.
Interviewer/Host
You've heard they're both phallic sympath. We should rethink the whole phallocentricity of this conversation. But it's patriarchy. What can we do? We're operating within the system, but it is totemic. And I imagine you get lots of 20 somethings feeling a bit lost coming to you for advice or wisdom, and I wonder if you feel the pressure of that.
Phoebe Waller-Bridge
I don't feel the pressure of it because I feel like it's not about advice or wisdom. It's about people feeling seen and people feeling heard. And it's more people coming up and going, I am fleabag. Or I understand that and it's men as well. But I feel like it's the duality of that character that has spoken to women in particular, which is the front that we have, which is we're totally in control and we have our nice haircuts and our red lipstick and underneath, like we have no idea what's going on. We contradict ourselves relentlessly. We have dark, perverted thoughts and then we sanitize them, even for ourselves. And we have impulses that are very similar to the narrative of male impulses, and yet they're not spoken about so much. I felt it was cathartic for me to have so many people say, oh, that's like me. Because to be honest, when I was writing it and with my theatre company, Drywright, and with five of us women creating that show through the producer and the stage manager and Izzo, my sister, the composer, and Vicky, the director, it felt so relevant to all of us and so funny for all of us. Like every time that I'd be like, playing around with something, if they laughed, I was like, okay, I'm not alone. And it was conversation that we had just before it went up to Edinburgh. And I was like, if this fails. Keeping on point. If this fails, then it essentially means that we're alone because it feels so right for us. And so the fact that it caught on and people could relate to it made us all feel less lonely. And me too.
Interviewer/Host
This brings us on to talk about Sheeza's, which was your third album.
Lily Allen
Yep.
Interviewer/Host
And I hesitate to talk about it in the context of failure because, not that it wasn't a great album, but I think how you perceived of it definitely in the book was something of a failure because you didn't feel you were being true to yourself. Is that right?
Lily Allen
Well, I think there's a bit of that. But then also I think that the tabloids were writing about me as if I was a massive failure at the time. So it's only so much telling yourself that you're doing okay when everybody's saying, haha, you used to be this successful and now you're half as successful, so you're a failure. I do think when I was writing that record, I probably was suffering with. Well, I was suffering with postnatal depression. And it's the first time that I'd approached a record in terms of it being a job and a means to an end that hadn't happened before. And what came out in terms of the material was I think it was decent, but it just wasn't great. And everything I'd done before was great. So, yeah, I don't know, I just lost faith in it halfway through. And I think there were a lot of contributing factors to that. I think I was struggling with being away from my kids for long periods of time when I'd spent a good three years just focusing on them and having them. And then suddenly it was like, you're yanked away. Don't talk about that. Because you're a pop star. People don't really want to hear about babies and vaginas and things like that. So, yeah, let's keep that to a minimum. And you should be back in shape as well, you know, which was hard. Basically meant sort of starving myself. So I was a bit mad from not eating. Then alcohol became an issue and drugs and sex. Yeah, I just. I think I have lived life to the extremes from a very young age. And I achieved a lot in my early 20s. And I think I maybe sort of had my midlife Crisis in my late 20s. You know, life as a female pop star is actually quite short anyway, so it kind of makes sense that.
Elizabeth Day
Yeah, it does.
Lily Allen
They don't tend to last throughout their 30s. So I guess if you applied that career to any other normal person, then, yeah, your late 20s sits about right in terms of midlife crisis.
Interviewer/Host
During this time, your marriage was breaking down. And I wonder if, as someone who historically identifies as a codependent, you were trying to end it in ways that you didn't have to confront it. So you were going out and having sex with people and do you think that's what was going on?
Lily Allen
I'm not sure. I mean, I've just come back from tour in America, which is where I was when things went wrong with me and Sam. And the same thing happened in my current relationship, you know, I mean, I didn't take loads of drugs and have lots of sex with other people, but I think that people deal with touring and stuff differently. And I'm a real home person, you know, I love my home comforts and I, you know, love my children and I love routine. And so to be taken out of that and be on a tour bus in the middle of nowhere without that sounding board and that person to talk to every day, yeah, I just became very lost. Touring throws up all these weird sort of existential questions anyway. You know, like when you're getting ready to go on tour, it's all about packing, making sure you've got everything that you're possibly going to need for that long period of time away. And then two or three weeks into it, you're like, well, what am I doing here? I'm here because this is my job and this is how you're going to pay off your mortgage in a house that you can't live in unless you're not living in it, if that makes any sense. But a couple of weeks later, you're like, well, actually, all I need is a backpack and a phone. Like, I don't need all the other stuff. Don't need the house. I certainly don't need. Need all the stuff that's in it. Like, it's all just. Yeah, because you're basically sitting on a bus for 22 and a half hours a day until you get on stage for an hour and a half, then it's all over.
Interviewer/Host
I've never even thought about it in those terms, like how. Yeah, how messed up that is. If I think just from my own perspective of how exhausting travel is just a flight, a long haul flight is and then to layer on top of that all of this other stuff.
Lily Allen
Yeah. And also because I guess like since streaming and stuff and since making an album and putting it out there is not enough now you can't live off of that. Streaming has completely devalued the product. So the one way in which to make money is to tour and the other way is branding. And the branding thing is a lot easier if you subscribe to the gym bunny makeup game. And the touring thing is not well suited to being mother of two small children. It just isn't when you're planning a tour and you're rooting a tour. And certainly on the Shees thing, I mean, it was better this time around because I had experienced it the wrong way. But this time around we built the tour around the kids half term so that they could come out to see me in New York and it wouldn't be six weeks away. It was only going to be two and a half weeks and then on each side. But it wasn't like that with Jesus. It was an experiment and it was a really fucking hard one. You know, I learned a lot from it, which was you're a mum and you're an artist and you've got to be really strict with the people around you in terms of making it clear that both jobs have to be done and be done well. Because if you don't make that clear, nobody else is going to take that into account. They just want to get you around whichever country you're touring in the cheapest way possible, in the most profitable way.
Interviewer/Host
There's a great song on your fourth album, no Shame, which I absolutely love. And we were chatting before we started this podcast about whether I'd listened to the album before I read the book and I had just for my own pleasure and recommended it to lots of people and then did the embarrassing fangirl thing of tweeting about it. And then Lily Allen liked my tweet.
Lily Allen
Hey.
Interviewer/Host
But part of the reason I love that album so much is not only the quality of the sound, there's just something about the way you sound and the samples you use that I love. But the lyrics are amazing. And there's one song, there's one song there. I've listened to it so much, Lily, honestly. Three, which is all about your then three year old daughter, about how you haven't had a chance to get to know her friends properly, how her social life is more full than yours and how today she made a papier mache fish mum, but you weren't around to see it and I It's such a beautiful song. Is that where it all came from? From this experience?
Lily Allen
There's a book actually might be here somewhere called like how to Listen so Kids Will Talk and Talk so Kids Will Listen. Much as I wanted to have kids, I've not really been around many children I don't have. I do have cousins, but they live in Wales and I wasn't around when they were little and my peers hadn't started having kids yet. You know, I was relatively young when I started tracking them out, I guess because I had postnatal depression and I was spending long periods of time away from them. I struggled with when I came back from tour to connect. Yeah, I just ended up in the studio writing one day and I knew that I wanted to have a song on the album about my kids, but I didn't know that it was going to come out like that from their perspective. But I love that song. They love it.
Interviewer/Host
Oh, do they? That's nice.
Lily Allen
They keep saying, like, when are you going to write another one?
Elizabeth Day
Please do follow how to fail to get new episodes as they land on Apple Podcasts, Spotify, Amazon Music, or wherever you get your podcasts. Please tell all your friends this is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening.
Phoebe Waller-Bridge
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Interviewer/Host
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Phoebe Waller-Bridge
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Lily Allen
Experian.
In this special episode, Elizabeth Day revisits favorite conversations with Phoebe Waller-Bridge and Lily Allen, focusing on their tumultuous, formative 20s. Both women reflect with brutal honesty and wit on mistakes, heartbreak, the pressures of gender expectations, and difficult moments in their careers. Their shared stories celebrate "failure" as a path to growth, creativity, and ultimately, wisdom. The episode is both entertaining and deeply human—a source of comfort and insight for anyone navigating their own messy decade.
Phoebe Waller-Bridge laughs at her “glorious” failures in romance, describing painful breakups, awkward one-night stands, and how these foster personal creativity:
Would she relive her 20s?
Sheeza’s Album & Feeling Like a Failure:
On Fast-Tracking Life:
Lily discusses the challenges of being on tour away from home and kids, and how touring exacerbated personal crises:
Hard lessons learned:
Warm, witty, candid, self-deprecating, and empowering. Both guests blend laugh-out-loud stories with moments of heartfelt sincerity and hope.
This episode offers invaluable reflections on navigating uncertainty, societal pressures, and self-doubt in your 20s. Both Phoebe Waller-Bridge and Lily Allen embrace their failures, revealing how vulnerability, humor, and honesty can lead not only to great artistry but to deeper self-acceptance. Elizabeth Day’s compassionate hosting brings out the best in both guests, making this a must-listen—or read—for anyone seeking comfort or solidarity in the chaos of figuring things out.