Dating Failures Before Cash

Toni Laites made history last year as the first American to win Love Island, but her journey to the villa was anything but ordinary.

Discovered in Las Vegas working as a cabana girl by the show’s creative director, Toni was persuaded to fly 6,000 miles to Mallorca. The rest, as they say, is history.

But you don’t need to be a Love Island superfan to love this episode. Toni is funny, emotionally intelligent and disarmingly honest. She opens up about living with the chronic illness Ulcerative Colitis, her pattern of choosing the wrong men in the past, working through anxious attachment and the hard-won strength it takes to forgive yourself.

This is a conversation about resilience, self-awareness and what it really means to back yourself - even when the odds (and the public vote) are against you.

✨ IN THIS EPISODE:

03:18 Vegas Sales to Villa Casting

05:36 Saying Yes to Love Island

07:21 Life Inside the Villa

08:33 Votes, Outcasts and Forgiveness

10:57 The Big Three Friendship

14:18 Health Scare and Ulcerative Colitis

28:10 Tourist In London

28:43 Toxic Dating Patterns

32:22 Pressure On Her Relationship

34:57 Fame And Social Media

37:34 Family And Attachment

44:28 Self Criticism And Hate

49:44 Plan For The Future

💬 QUOTES TO REMEMBER:

There is value in doing nothing and taking a step back and waiting for good things to come.

I always say not all disabilities are visible and people don't really understand what that's like.

🔗 LINKS + MENTIONS:

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

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

📚 WANT MORE?

Olivia Attwood - on heartbreak, public scrutiny and building a successful career after Love Island.

Jessel Taank - on infertility, identity and The Real Housewives of New York.

💌 LOVE THIS EPISODE?

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👋 Follow How To Fail & Elizabeth:

Instagram: @elizabday

TikTok: @howtofailpod

Podcast Instagram: @howtofailpod

Website: www.elizabethday.org

Elizabeth and Toni answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com

Production & Post Production Coordinator: Eric Ryan

Engineer: Matias Torres

Assistant Producer: Shania Manderson

Senior Producer: Hannah Talbot

Executive Producer: Alex Lawless

How to Fail is an Elizabeth Day and Sony Music Entertainment Production.

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