ON EMBARRASSING MOMENTS… With Dan Levy and Phoebe Waller-Bridge

3 Nov 2025 · 12 min

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In short

How To Fail With Elizabeth Day - Episode Summary

Podcast Title How To Fail With Elizabeth Day

Podcast Description A podcast that celebrates failures and the lessons learned from them, featuring weekly guests who share their personal failures and insights.

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Episode Title ON EMBARRASSING MOMENTS… With Dan Levy and Phoebe Waller-Bridge

Episode Description This episode revisits some of the most entertaining embarrassing moments shared by guests Phoebe Waller-Bridge and Dan Levy. The discussion aims to bring lightness and humor to the universal experience of embarrassment.

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Key Moments & Discussions

Phoebe Waller-Bridge's Apple Crumble Incident

  • Context: Phoebe recalls a moment while filming *The Iron Lady*, when she was excited to interact with Meryl Streep.
  • The Incident:
  • Meryl, in character, approached Phoebe, which led to an awkward interaction.
  • In her excitement, Phoebe flung her apple crumble onto herself, leading to embarrassment.
  • Takeaway: The humor in failures and their lasting memories, as the apple crumble anecdote remains a favorite among fans.

Dan Levy's Birthday Cake Disaster

  • Context: Dan shares a childhood memory revolving around his birthday celebration.
  • The Incident:
  • On a day meant to celebrate his birthday, Dan tripped and dropped his cake in front of his classmates.
  • In a panicked reaction, he started eating the cake off his shoes, which further intensified his embarrassment.
  • Reflection: This moment is viewed as a formative failure that shaped Dan's understanding of embarrassment and social dynamics in school.

Themes Explored

  • Embarrassment as a Shared Experience:
  • Both stories highlight how everyone experiences embarrassing moments, regardless of their success.
  • The importance of laughter and humility in dealing with failures.
  • Childhood and Identity:
  • Dan and Phoebe reflect on their school experiences and how early failures impacted their self-perception.
  • The conversation explores how childhood failures can shape one's path in life and career.
  • Humor in Failure:
  • Both guests emphasize the fine line between observational and cruel comedy.
  • The discussion encourages embracing failures as part of personal growth and storytelling.

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Key Takeaways

  • Universal Nature of Embarrassment: Everyone has embarrassing moments that can be laughed at and learned from.
  • Growth Through Failure: Sharing failures can foster connection and understanding among people.
  • Impact of Early Experiences: Childhood failures often resonate throughout one's life, influencing self-identity and career choices.
  • Comedy as a Healing Tool: Humor helps to navigate and reclaim experiences of embarrassment and failure.

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Links & Mentions

  • [Listen to Phoebe Waller-Bridge’s full episode](https://link.chtbl.com/Xr_yQtIZ)
  • [Listen to Dan Levy’s full episode](https://play.megaphone.fm/b0cje4y2thgpbbpms2q64w)
  • [Join the How To Fail community](https://howtofail.supportingcast.fm/#content)
  • [Elizabeth’s Substack](https://theelizabethday.substack.com/)

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Follow Elizabeth Day

  • Instagram: [@howtofailpod](https://www.instagram.com/howtofailpod/) | [@elizabday](https://www.instagram.com/elizabday/)
  • TikTok: [@howtofailpod](https://www.tiktok.com/@howtofailpod) | [@elizabday](https://www.tiktok.com/@elizabday/)
  • Website: [www.elizabethday.org](http://www.elizabethday.org)

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Transcript

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0:00The Loose Women podcast is back and this time we've shaken things up a bit. in Loose Women Just Between Us we'll be asking you to send in your juicy problems and dilemmas for our consideration then every week you get two of your favourite Loose Women or us and what we all try and do is help you solve your problems just by drawing on our own life experience and there's a lot so why don't you come and join us just search Loose Women Just Between Us wherever you're listening to this podcast it's Jonathan Van Ness from getting better with Jonathan Van Ness it's easy to feel hopeless but we don't have to stay there I'm all about finding places where we can turn that energy into hope and into action one of those places is Americans United for separation of church and state Americans United or AU is this quiet but mighty force working every day to preserve freedom without favor and equality without exception I am so obsessed with that tagline and let me tell you something, honey.

0:59That wall between church and state, paper thin. It's got a leak, honey. It's one of the last safeguards protecting so many of our rights. So right now, from bodily autonomy to LGBTQ plus rights to the future of public schools, to me, this is about creating a world where everyone gets to live as themselves as long as you're not harming anyone else. Now is not the time to curl up and hide. It's the time to link arms and stand together for a better future. Join Americans United for separation of church and state and their growing movement. because church-state separation protects us all. Learn more and join the fight at au.org slash better.

1:34Let's go, Americans United!

1:45Welcome back to this week's archive episode reflecting on some of the best bits from How to Fail's past. This week, we're keeping it light and taking a look at some of the funniest and most entertaining embarrassing moments from guests on How to Fail, starting with the one and only Phoebe Waller-Bridge. This is honestly one of the most hilarious moments, listening back to Phoebe talking about trying to impress Meryl Streep and her body sort of malfunctioning. And all I need to tell you, because you might have heard it before, is that it involves an apple crumble. I've lost count of the number of times listeners have come up to me at live shows and said, that apple crumble story, and I know immediately what they're talking about.

2:27It's one of those anecdotes that gets better every time you hear it. Then Dan Levy talks about a birthday cake failure he remembers vividly from his childhood and the humiliation he felt at his knee-jerk response to dropping it. I hope this episode brings some light to your day and reminds you that we all have embarrassing moments, whoever you are. First, it's Phoebe and the apple crumble.

2:55I was really excited to meet Meryl Streep when I was doing The Iron Lady Was she? I was weird with her though I go weird around celebrities and always in a very individual way for each celebrity I should just not be around them What did you say to Meryl Streep that was weird? Well Meryl Streep was doing The Iron Lady and she was in this prosthetic sort of whole body face scenario the lights were so hot so whenever she was on set she didn't she couldn't really speak in between so much energy was taken up and just like acting through this you know mask and everything so when the light so she would never say anything in between cuts and we always knew and she was always like i'm really sorry but i just can't i knew i just need to like power down have a glass of like sips and water through the straw but there was one day when uh the lights went off they called cut and then she just turned around to this room of people and went you know in her margaret thatcher voice and just went hey how's everybody's day and everyone just freaked out everyone's like froze in the room because they were like oh my god everyone at the same time like we were like vultures just like this is our moment to have to share words with Meryl Streep and uh so everyone sort of was being very casual and it was the scene was like a drinks party or something but edging towards her with this kind of wild look in their eye and everyone was trying to have some some personal bants with uh with Meza so she was just opening the conversation and then it was getting like really competitive and we were like crowding around her but everyone was trying to be very casual and then she started up this conversation about something anyway I tried a joke and it landed and she laughed and she was like oh everyone else looked at me with steel and an ashen face and fury and I was like I've won it she's mine she's mine so she was mine but after that I was like she's totally mine she's totally mine we're gonna have a day together we're gonna like like nod to each other respectfully in the corridors we're gonna we may even like you know graduate to a drink at some point and then um at lunchtime I was sitting at this table with everybody and I was eating this apple crumble and she came down the stairs she was feeling lively this day uh obviously outside of the prosthetic she came down the stairs and she was walking towards me I was like oh my god oh my god like she's gonna come to the table and we're friends now because I was the one that made her laugh and she walked up to the table and she put her hand on my shoulder and she said uh oh what are you eating I've never understood why this I got so excited about the banter with Meryl that I flung my apple crumble straight into my chest.

5:17My costume chest. And I literally squawked, MY APPLE CRUMBLE! And she went, oh. And then she went back to her American accent, which she hadn't done for the whole time. And she went, I wasn't going to take it from you. And I was just holding this awful dripping pudding over my beautiful silk shirt. And I'm just holding it there really tightly, not letting it go. I was just like, oh my God, everyone's doing it. I'm like, what was that? That was the strangest response. And then she was like, okay. And then she moved off and then I had to go and apologise, costume thing, get my shirt. So just weird stuff like that.

5:55You made her break character. You made Meryl Streep break character.

6:03Your first failure relates to a time in second grade, which for UK listeners is when you're about seven or eight years old? I would think so. Yeah. It's like kindergarten for a couple of years and then first grade and second grade. So I don't know what that... Yeah. So what happened? I bring this up as a failure because sometimes, you know, there are these snags in our memory where we stick on these moments and they should have just come and gone. And yet they are as vivid as the day it happened. And the earliest huge failure for me was, it was my birthday, except my birthday's in August. So we, you know, you're very young and you want to celebrate with everybody because everybody who has a birthday during the school year gets to have cake and thing.

6:51So my mom made me a cake to bring in right as the school year started in September in Canada. So we did a celebration around my birthday because it's in August. And I was feeling a little embarrassed anyway because it wasn't really my birthday, but it was, anyway. The cake is at the back of the classroom My teacher says, we have a surprise for the class. I knew what the surprise was. And she said, Daniel, I'm going to go and get the cake. And I said, no, no, no, I can get the cake. I'll get the cake. Very excited. Happy to share with the class. The cake is revealed. The class is excited. Just as I get to the front of the classroom, I trip and the cake falls out of my hand and onto my shoes and flips sort of cake first onto the ground.

7:34And the class obviously is hysterically laughing. And it is the deepest humiliation I'd felt in my young life. And I looked around and didn't know what to do. And it's that time where you're young and you don't know whether you should cry or laugh. And so my reaction was to sort of, I guess, go completely pale in the face and then reach down and start to eat the cake off my shoes. I don't know what that impulse was. I think it was kind of panic and deep embarrassment. And it was a moment that I've remembered because, in a way, I've kind of intellectualized it as like the first exertion of hubris or something.

8:19Like, I was like, no, no, no, I got the cake. You don't need to get the cake for me. I have it. And I didn't. I was too young. My hands were probably too small. The cake was too heavy. All of those things. And then it just, it was a symbolic thing, I have to say. It's so interesting to me how many people on this podcast do choose moments like that from their early childhood where they embarrass themselves. And I think it's that thing of when you're a child and you're trying to work out who you are in this confusing world, and you don't know whether someone is making fun of you or is on your side, it can feel quite terrifying.

9:00Yeah. And I, a bit like you, I didn't have the happiest school experience for various reasons. And I wonder what you were like after that as a child at school. What was your school experience? I just, to me, I look back, I've never liked school. Me neither. Not a single day. And I think part of it had to do with the fact that I wasn't the truest expression of myself. and I think when you're playing a part, it gets exhausting and you don't like yourself because you're hiding yourself. In my particular case, I just wanted to get through it because I think in my mind, I thought once school is done, people will have the maturity to accept me.

9:43I think it was toward the end of the last year of my high school experience that I told some friends. It wasn't a safe space. It's a... I mean, it's tough. And I think also when you're the butt of the joke or you are bullied, it makes sense to me that you now write the jokes. Yeah, of course. You want to be in control of when people laugh. Yeah. I didn't think of it that way. But now that you bring it up, it makes sense. Yeah. And also, yeah, a control of and also how the jokes are formed. And I think the one thing I learned from both my dad and Catherine O 'Hara during the creation of Schitt's Creek was you can tell very funny jokes about people in celebration of people, but not at their expense.

10:32And there's a very fine line between cruel comedy and observational comedy. And I will always lean towards observational comedy. The roast sort of world of it all is its own subculture, which is something I would kill for the self-confidence to endure. I also think that's why shit's worked. Because there was a warmth to the comedy and everyone was laughing at themselves as well as everyone else. There was a kind of democracy of comedy across the board. There was no butt of the joke. And that will always be something I'm trying to rewrite through my whole life, I think, through anything I do is the kind of reversal of the first chapter of my own life, I guess.

11:34Thank you so much for listening.

From the publisher

Welcome back to this How to Fail episode where we journey through the archive to revisit some of the best bits. This week we’re keeping it light and taking a look at some of the funniest and most entertaining embarrassing moments on How to Fail.

You’ll hear from Phoebe Waller-Bridge, originally released in July 2018. Phoebe talks about trying to impress Meryl Streep and her body sort of malfunctioned… involving an apple crumble!

Then we hear from Dan Levy, from his original episode in January 2024. Dan talks about his birthday cake failure from his childhood and the humiliation at his knee-jerk response. I hope this episode brings some light to your day and reminds us that everyone experiences embarrassment at some point!

Listen to Phoebe Waller-Bridge’s full episode of How to Fail here: https://link.chtbl.com/Xr_yQtIZ

Listen to Dan Levy’s full episode of How to Fail here: https://play.megaphone.fm/b0cje4y2thgpbbpms2q64w

🔗 LINKS + MENTIONS:

Elizabeth’s Substack: https://theelizabethday.substack.com/

Join the How To Fail community: https://howtofail.supportingcast.fm/#content

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Website: www.elizabethday.org

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