ON NAVIGATING YOUR 20s... With Phoebe Waller-Bridge and Lily Allen

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2:08Welcome 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.

2:48First 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 sheasers 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.

3:34Do you think you failed at relationships in your 20s? Oh, yeah. Yes, gloriously. I mean, I think even when you first said to me, this is a podcast about failure, 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 horrible sticky one night stands or whatever it is, something you grow in those moments.

4:18And so I value them all. 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? Let me flick through my diary. Your Rolodex, your extensive Rolodex. I wish I had a date diary. And that actually would be proved 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.

5:02and 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 Etta James's At Last. I'm always singing it like I mean 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 and he was like um I didn't realize this had meant so much to you I was like oh god no god no no um that was that was pretty dire that led on to a very uh an awkward breakfast.

5:50I mean, they all sort of feel gloriously muddy. See if I can think of another one as we go along. Are you glad that you don't have to live your 20s again? Yes. Like, there's a brilliant line in Girls when 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 Dunham'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 I prefer my heart and my guts now. I mean, your skin's amazing.

6:21That sounds like such a creepy thing for me to say right now. But you're bathed in the evening sunlight of East London. Do you remember when we got quite pissed off one night and I was going, I used to have a porcelain forehead. Alabaster. Alabaster. Like alabaster. Alabaster boy. 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 we're 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 you realize actually no this is just there's a 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.

7:16And then that flicked my rebellious switch even more. And now I just feel way more fierce than I ever did in my 20s. When you say it's a question of control, do you think it's control that stems from men having been in charge? Yeah, yeah, absolutely. I mean, I can't imagine that women en masse operating at that level would want to peddle 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. 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.

7:50And probably on some level men are as well. But I feel like it's just a habit that we need to break. And I have faith that we will as more women climb higher up that pole. Do you feel... Don't swing higher up that pole as we do. We reclaim the pole. do you feel because Fleabag has been so totemic for so many women particularly young women in their 20s didn't say pole she said totem so much classier way I've been I've been swinging my body around that totem as much as I possibly can we've heard they're both phallic symbols we should rethink the whole phallocentricity of this conversation but it's patriarchy what can we do we're operating within the system um but it is totemic and I imagine you get lots of 20 something things, feeling a bit lost, coming to you for advice or wisdom.

8:41And I wonder if you feel the pressure of that. 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 company dry right and with five of us women creating that show through the producer and the stage manager and Izo 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 a 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.

10:11This brings us on to talk about Sheezers which was your third album 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 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? 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 OK when everybody's saying, ha ha, you used to be this successful and now you're half as successful, so you're a failure.

10:47I do think when I was writing that record, I probably was suffering with, well I was suffering with personal 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 um but it just wasn't great and everything I'd done before was great um 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 you know 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 you know and then suddenly it was like you're yanked away and all don't talk about that people 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.

11:48So 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 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. 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 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.

13:33And 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. I don't need the house. so I certainly don't 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, and then it's all over.

14:09I'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. 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 Jim Bunny make-up game and the touring thing is not well suited to being a mother of two small children.

14:48It just isn't. When you're planning a tour and you're rooting a tour and certainly on the Sheezus 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 your mom 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.

15:31They just want to get you around whichever country you're touring in the cheapest way possible, the most profitable way. 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. 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.

16:08But the lyrics are amazing. And there's one song, you know, 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-mâché fish mom but you weren't around to see it yeah and I it's such a beautiful song is that where it all came from from this experience um there's a book actually I 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 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 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 oh do they that's nice they keep saying like when are you going to write another one please do follow how to fail to get new episodes as they land on apple podcast 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 Limu, Limu!

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