The ‘How to Fail’ podcast host has recently launched a new project: ‘How to Date’. But how do her heartbreaks’ past inform the lessons she teaches? 

Elizabeth Day has built her career on failure. The most prominent “failure” of them all being heartbreak. “Heartbreak informs everything that I do,” she declares. 

The author-slash-journalist started her award-winning ‘How to Fail’ podcast in response to the heartbreaks she suffered: “failing” to maintain her marriage, “failing” to know herself and “failing” to have children. “The story of my dating life is kind of the story of failure,” she grins, now happily in a relationship. 

Talking over Zoom, she looks far from heartbroken today. A knitted red top twists around her thumbs, while a glass rose peeks out from her shelves. Her iconic bob is chic-ly short. 

“I really thought I knew myself because I’d done 12 weeks of therapy” 

Her latest endeavour, the ‘How to Date’ podcast co-hosted with Married At First Sight relationship expert Mel Schilling, is her most heartbreak-fuelled project yet. It chronologically teaches its listeners how to re-enter the dating world post-breakup. 

Question one of the series: “Are you even ready to date?” 

“That’s where I went wrong,” she laughs. “I definitely should have got to know myself better.” Now aged 46, she describes her 30s as a period of “intense transition” which culminated in her getting married (and then divorced) to the “wrong person”. The person in question being journalist Kamal Ahmed; she realised that she wanted children and he didn’t. “I really thought I knew myself because I’d done 12 weeks of therapy.” 

At age 36, she was single for the first time since she was 19. “Spoiler alert!” she leans in as if confessing a secret, “it’s not an ideal time for a cis straight woman to be single.” 

Having been a serial monogamist her entire adult life, she shape-shifted her way through her relationships: “I became smaller and smaller”. Referencing the “cool girl” passage in Gillian Flynn’s Gone Girl, she felt pressure to be the girl who “hangs out and knows the offside rule, who is super chill and looks great in their cut-off t-shirt.” On the other side of the coin, she sought to embody the serene hostess type who could have loads of people around for Sunday lunch and whip up a roast at a moment’s notice. 

“And actually, I’m neither of those things,” she confirms with a firm shake of her head. 

Her heartbreaks have taught her that being a people pleaser is not a gateway to having a fulfilling relationship. Growing up in the 80s and 90s, she felt “socially conditioned” to put others first. “I think kindness,” she says with slow precision, “is the most magnetic and important characteristic anyone can have, but I took it to an extreme where how other people thought of me was way more important than how I thought of myself.”

Having broken and grown into the present version of herself, she’s learnt that the things she thought of as flaws “are part of what the right people think are loveable in me”. While all heartbreaks are, of course, “challenging”, for Day “if you’re strong enough, it’s a game changing process to go through. It’s a sort of immersion therapy in getting to know yourself.”

“I’ve got a lot of mileage out of terrible dating stories that are now super entertaining”

While she talks with self-assured confidence, unphased by the well-worn pains of the past, she still remembers the aches they caused. “I think heartbreak is one of the most difficult forms of grief […] I remember every single heartbreak I’ve ever suffered and they really made me question who I was but also who I thought the other person was.” 

Following her divorce, she fell in love with a younger man – Phoebe Waller-Bridge’s younger brother, of all people – only for him to break up with her just three weeks before her 39th birthday. In her book How to Fail she candidly outlines how angry the sudden split made her – angry at him for leaving, angry at herself for thinking it would work. 

Over the years, heartbreak has integrated itself into Day’s brand (“I hate the idea of having a brand”), but she views the association as more of a gift than a burden: “I’m very motivated by putting work into the world now that I would have wanted.” 

Through her podcasts and her writing, Day realised that the most embarrassing and uniquely personal stories often tend to have the most universal resonance. From getting ghosted by her now ex-friend to the earth-shattering pain of her miscarriage, Day has discussed heartbreak in all its forms. “The amazing thing is that I get people coming up to me and saying, ‘Oh my gosh, I felt the same. Your work has helped me’. It’s actually really empowering.” Plus, as she so aptly puts it, “I’ve got a lot of mileage out of terrible dating stories that are now super entertaining.”

“I am a firm believer in the idea that rejection is redirection”

She recently published an article in The Times about a man under the pseudonym of Freddie – a post-breakup fling. Freddie rocked up to their late night sleepover with a camp bed in hand. Waking up in a cold sweat to the sight of him sleeping on her floor, she was consumed by horror at the idea of taking this man to be her lifelong partner. She broke things off the next morning. To which he responded: “As long as you don’t change your mind in six months because by then your ovaries will have dried up and I won’t be interested.”

Through discussing her heartbreaks so openly, she has amassed a dedicated following of lonely hearts looking for advice. And it’s easy to see why. There is a warmth to her presence, approaching each challenge with the plucky positivity of a life coach (“You’ve survived that! That’s amazing!”). Though she feels pressure, she thinks it’s appropriate for the task. “If people trust me in a moment of vulnerability, I would never take that for granted.” She holds her hands together in deep sincerity. “I’m incredibly honoured that anyone would come to me […] I like the idea of being someone’s big sister.”

Day certainly embodies the older sister aura. With her chunky gold jewellery and funkily striped (and ludicrously large) mug, it seems that she has finally got her life in order. There is a vibe of sleek perfection to her set-up: framed black and white photos, a splash of modern art and a fern creeping into shot. Well-versed in the language of heartbreak, each snippet of advice she offers is eloquently delivered and easily quotable. 

Asking her to flip her podcast on its head (introducing ‘How to Break’ – a title she promptly threatens to steal), she imagines the advice she would offer. The main lesson that she’s learnt? She is stronger than she thought. “I often say failure is data acquisition, and one of the pieces of data that we can acquire is that we can survive. To have that kind of experience to draw on is really comforting.”

Looking back at her pain, she is “grateful” to each and every heartbreak for their teachings. “That’s why I am a firm believer in the idea that rejection is redirection.” Each breakup you experience will “teach you something really meaningful in the fullness of time”.

“And when you believe that, you realise that just because a relationship ends does not make it a failure.”