“I felt like a failure”: Elizabeth Day on what she learned from dating a younger man who broke her heart

We’ve heard a lot about the perks of a dating younger man – but is it really all it’s cracked up to be? For Elizabeth Day, author, dating guru and host of hit podcast How to Fail, it wasn’t. It did however, offer some important learnings.

Starring on the cover of Good Housekeeping’s June issue, Elizabeth explained how, in 2017, she was dumped by a younger man. He was nine years her junior and the relationship ended "out of the blue" just before Elizabeth turned 39. She felt, she shared, "like such a failure".

"I did what I now realise is a classic clichéd thing: my first major relationship after my divorce was with a younger man who was completely free of responsibility. We had two great years together, but ultimately, he was at a different stage in his life," she says.

The man in question, Elizabeth went on to confirm was in fact actor and screenwriter Phoebe’s Waller-Bridge’s brother, Jasper. Elizabeth had met Phoebe at a conference, and she shared how the pair bonded almost instantly.

"I went to Las Vegas to this four-day conference that sounded like hell. I hate networking, I hate conferences, but there was a competitive interview process [to join the Project] and I’m very competitive! Plus, it was a free trip to Vegas," she says.

At the airport, she was handed a document with biographies of the fellow delegates. "There was this woman called Phoebe Waller-Bridge, who’d had a sellout show at the Edinburgh Festival Fringe called Fleabag. I’d never heard of her, but her biography was really funny. I told her as soon as we landed in Vegas that we’d be friends – she said, ‘Great!’ On the coach to the hotel, we went straight in, sharing such deep stuff about our lives. I fell in platonic love with her."

Despite not finding success in love with Phoebe’s brother, there was a different kind of success waiting for Elizabeth on the other side of her heartbreak. In the wake of her break-up, Elizabeth couldn’t listen to music, so she turned her attention to podcasts. The first-ever podcast had been released in 2003 and by 2017, podcasts were having a moment, to say the least.

In 2018, Elizabeth went on to launch the hit podcast we now know as How To Fail with Elizabeth Day, funding the first few episodes by selling the wedding dress from her earlier failed marriage to Kamal Ahmed. The first episode featured Phoebe Waller-Bridge - of course - and seven years on, her guests have included the likes of Kate Winslet, Sharon Horgan and Mel B.

That wasn’t the only silver lining of Elizabeth’s break-up, either. In 2018, Elizabeth was considering moving to LA full-time when she was matched with a man on the dating app Hinge. He was insistent they meet, so in the morning she booked her flight and in the evening she went to a hotel bar to "get the date out of the way before starting my amazing future in California."

Only things didn't quite go to plan. Much to her surprise, Elizabeth found she had "immediate chemistry" with Justin Basini, a divorced father of three, who’s the co-founder and CEO of ClearScore, a financial tech company. She fell in love with “a thoughtful, honest, evolved man” and in 2021, Elizabeth and Justin got married.

“He first told me he loved me in [legendary LA hotel] Chateau Marmont, which was perfect,” she says. "From then on, it’s been amazing." It seems Elizabeth found her happy ending after all.

Read the full interview in Good Housekeeping’s June issue on sale from Thursday 24^th April.

How To Fail with Elizabeth Day is available wherever you get your podcasts.

Read the full interview in Good Housekeeping’s June issue on sale from Thursday 24^th April.

How To Fail with Elizabeth Day is available wherever you get your podcasts.