Elizabeth Day

How to Fail: Everything I’ve Ever Learned From Things Going Wrong


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who spent most of his twenties trying and failing to make it as an actor before turning his hand to writing, said that he now realised ‘there are ways out, that we’re not fixed at the age of twenty-two, twenty-three, that life is long and you can try things for a while and if they don’t work out, do something else’.

      But of course, it’s only when we’re older and have knocked about a bit that we can conclude there is no uncomplicatedly happy end point. There are a series of points – some happy, some sad, some simply quietly contented – and each one will be different from how we imagined it. Not better or worse; just different. And perhaps what surviving your twenties makes you realise is that life, after all, is texture.

      ‘I feel like I did it [my twenties], I committed to it,’ Phoebe Waller-Bridge said when I spoke to her about her own decade of transition. ‘I’d really like to have the skin from my twenties,’ she joked, ‘but I prefer my heart and my guts now.’

      That’s the thing. Because however much you might feel you’re failing at your twenties when you’re living through them, they are a necessary crucible. Your twenties are spices in a pestle and mortar that must be ground up by life in order to release your fullest flavour. By the end of them, you’ll have more heart and more guts – and you’ll know never to roast broccoli again.

       How to Fail at Dating

      My penchant for long-term relationships throughout my twenties culminated in a marriage that didn’t last. When I got divorced at the age of thirty-six, I found myself single and clueless, having never really been on any dates.

      I got my first serious boyfriend when I was nineteen, and for the next seventeen years spent much of my time traipsing across London with hair-straighteners, a travel-sized pot of face-cream and clean knickers stuffed in my handbag to stay over at my other half’s. God, those trips were exhausting. Schlepping around on the tube, always having to think about the next day’s clothes and whether you could fit your gym kit in your rucksack. I honestly think that one of the main motivating factors for moving in together is the simple joy of having all your stuff in one place.

      When I got divorced I found that, in the two decades during which I’d been attached, dating had undergone a seismic change. Meeting someone online was no longer perceived as being slightly weird and desperate. Swiping left on Tinder was the new normal. When I suggested to my friend Francesca that I could meet someone in the conventional way, by catching their eye across a crowded room, she laughed.

      ‘No one meets anyone in bars any more,’ she said gently, as if explaining a new-fangled machine called a computer to an elderly Amish lady wearing clothes made out of sackcloth.

      The idea of online dating terrified me.

      ‘What if I meet an axe-murderer?’ I asked Francesca.

      ‘Well you’d be more likely to end up with an axe-murderer if you randomly met someone on the street,’ she argued. ‘At least online you can read their profile, get a sense of who they are and what they want out of life.’

      It was a good point.

      And so I signed up to Bumble, the app that is meant to give women control over dating. Once a match has been made on Bumble (you’ve swiped right on each other’s profiles because you both like the look of each other), it’s up to the woman to initiate first contact. You might think this sounds empowering and dynamic. In reality, it just means you’re forced to come up with some witty first comment to attract a man’s attention, and then feel personally rejected when they don’t respond. So much of online dating is based on ‘banter’ that you spend half your time on the sofa feeling like you’re writing the sub-par script for a Carry On film. I made so many sexual innuendos during this period of my life that it became worryingly second nature. You could barely say anything involving the words ‘box’ or ‘balls’ without my lapsing into a breathless flurry of double entendre. I was the winking emoji face made human.

      Frequently, a connection made on Bumble just turned into an extended exchange of filthy jokes and then a sudden lapse into silence. But I did get a few real-life dates, each one slightly more disappointing than the last. The first was with a man called Kenny who had just done the Hoffman Process, a course that essentially seems to be a psychological detox, although no one who has been on it is really allowed to talk about what happens, other than to say how amazing it was and how it, like, totally changed their life. Kenny stared at me with dilated pupils and spoke to me with the zeal of a born-again Christian. He touched me frequently on the hand and when I said I needed to go to the loo, he claimed he did too and followed me to the toilets. Kenny was intense. At the end of the evening, Kenny immediately arranged a second date, which a few days later I found an excuse to postpone indefinitely.

      Then there was Alec, who WhatsApped me hand-drawn pictures of flowers before we’d even laid eyes on each other, which was sweet, but then we met and I didn’t fancy him and the next day he messaged saying he’d written a song about me and it all seemed a bit much. There was the guy who spoke on the first date about how his last relationship had ended because his partner had gone through several rounds of IVF and how difficult it had been … for him. There was the lawyer who quoted the spiritual teacher Deepak Chopra and then sent me several links to YouTube videos featuring Deepak Chopra and followed up with a bevy of Deepak Chopra quotes. I love a bit of Deepak Chopra but even I have a saturation point.

      I expanded my remit to include other dating apps. OK Cupid was terrible: full of men who took selfies from an unflatteringly low angle while driving their cars, or while half naked in the reflected gloom of a hotel mirror, the flash rebounding harshly off the walls of a Premier Inn somewhere in Basildon. There were men who posed with motorbikes or with dogs, or with sweet-faced children (‘Not my own!’ the caption would read) or skiing or hiking or casually knocking up a home-made pasta dish, as if to show they encapsulated all the things one most desired in modern masculinity.

      Then there were the outliers: the bespectacled dwarf in a waistcoat wielding a large serrated knife who had swiped right on me; the man whose profile photo depicted him posing in front of the Arbeit Macht Frei gate at the entrance of Auschwitz; the guy whose first message to me was ‘Hi, why don’t we get married?? It’s a nice idea isn’t it?’ followed by the grinning face emoji with one eye closed and tongue sticking out.

      My friends would be in stitches when I recounted all of this and it’s true that one of the great things about failing at dating is that it gives you so many entertaining anecdotes. Phoebe Waller-Bridge was inspired to write much of Fleabag by a string of romantic failures in her twenties.

      ‘I think fighting so hard to be so in love with someone with all that passion in your twenties and teens and then throwing everything at it and it’s not working, or there being so much pain … that is the stuff that so much creativity comes out of, so it’s out of those painful break-ups or miscommunications or just horrible sticky one-night stands or whatever it is: you grow in those moments and so I value them all … I wish I had a date diary. That actually would prove very useful now.’

      When I asked her to describe the worst date she’d ever had, Waller-Bridge replied: ‘There’s just the ones where you just don’t click at all. You feel yourself falling slowly into a chasm of boring the other person to tears.

      ‘There was one when there was a guy. We had a couple of dates and then he’d stayed over and the next morning, it was quite clear to me that this wasn’t going to go anywhere, and I think for him as well. But a song I really love is Etta James’s “At Last”. I’m always singing it. It’s just the earworm that I always have. And I remember I was living in a flat that was on the fifth floor or something, and 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, like, “My looooove has come alooooong …” And when we got to the bottom of the stairs he was ashen-faced and shaking. And I was like, “What?” and he was like, “I didn’t realise this had meant so much to you.” I was like, “Oh God no, no!” That was dire. That led on to an awkward