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Gail’s story

When I was last briefly single in 1994, John Major was Prime Minister, Love Is All Around by Wet Wet Wet dominated the airwaves, and the World Wide Web was in its infancy.

I was 35, owned my own flat in Chelsea, was fashion editor of a national newspaper and my social life was filled with parties, weddings and weekends away in the countryside. If dating sometimes seemed hard then, it certainly never occurred to me that I would find myself in a similar – but simultaneously very different – situation later in life.

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Fast forward to today and, once again, I am single, and the process of finding a new partner is both daunting and baffling. There is a whole new world of dating apps and ways of finding potential suitors that did not exist 24 years ago. In my dating heyday, there was nothing more thrilling and wonderful than catching the eye of a man across a room, that sudden smile that indicated mutual interest, the spine-tingling expectation as he walked towards you and the love story that would hopefully follow. Online dating, however, seemed to be all about instant gratification. How could a few photos and a miniscule profile allow you to make a judgement on whether you have anything in common with someone, let alone if you could fall in love with them?

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But when Vogue asked me, on my 60th birthday, to be part of a generational dating swap, I was genuinely excited. In the two years since I ended a 21-year relationship, I had not even dipped a toe into the dating game – online or off. My mission? To step into the dating shoes of a millennial, using only my phone to meet and date as many men as possible within two weeks. In the meantime, my very youthful counterpart, 22-year-old Vogue staffer Soey Kim, was to turn the clock back to the 1980s, employing all the conventional ways of meeting a man that were instinctive and natural for my generation.

Before the experiment, Soey and I set each other a number of rules, mine being to only use social media and dating apps to meet a man, as well as to track down an ex-boyfriend from my past (who hopefully would be single) and suggest we meet for a drink/lunch/dinner. Another instruction was to deviate from my relatively old-fashioned concept of dating and to do something brave that might introduce me to a man.

My first task was to create profiles on Tinder, Bumble, Hinge and Happn. While not in the movie-star handsome category, my first date (from Bumble) was the right age (56) and stated “chairman” as his job title – and, on paper, we had many things in common. As I nervously entered the Notting Hill pub in which we had agreed to meet, it was obvious that his photographs were many years out of date. In all honesty, I would hardly have recognised him if he hadn’t recognised me. Quite apart from the misleading photographs, he had neglected to point out that he had been married three times, while on the topic of the chairmanship he seemed slightly ambiguous. I came away disillusioned and despondent. I’d known it was unlikely that I was going to find a life-long partner at the first attempt, but it still made me rather melancholy.

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Nonetheless, Bumble provided me with many more men over the coming days. I got braver, swiped right more than I had done to begin with, had over 50 likes and an age range that spanned from 42 to 62 (when I pointed out to one 42 year old that I was 60, his reply was, “So?”). On Tinder, I only managed a few messages with someone that came to nothing; Happn didn’t happen (do any men in west London use it?); while on Hinge, I met one suave silver fox whom I naively thought was charming until one unsolicited picture arrived in my inbox. All I can say is I suppose I ought to take it as a compliment that I had stirred feelings in his trousers, but I did not take up his invitation to visit him that evening to provide much-needed TLC.

Like real life, dating apps come with their own social etiquette, or lack thereof. The whole ethos is more brutal. This is man or woman hunting at a serious level, with no rules or guidelines. With no face-to-face contact before a date, and no friends in common, it is so much easier to ignore the usual mores of society. Men who had earnestly messaged me suddenly vanished into the ether. This, I discovered, was called “ghosting”. It happened a lot, and I swiftly learned to brush off the rejection and move forwards. It is, I’m told, bad etiquette to follow up after you have been ghosted, but when a handsome type disappeared after a single message, I tried again. Twice! There was radio silence for three weeks, until one morning, a message popped up. His reply was gentlemanly, with a genuine apology for his rudeness. A case of bad timing, he said.

It was so much easier than I thought to track down a previous boyfriend. Nick* and I had dated for six months in the 1990s, but the relationship had fizzled out with no regrets or animosity. I hadn’t seen him for more than 25 years, but it took me less than 30 seconds to find him on Instagram. I saw he had his own business website, which helpfully listed his mobile number. Taking a deep breath, I dialled it. He answered and, over the next hour, we talked as though the intervening years had never happened. When we met at my favourite restaurant (that he picked) a few days later, he looked even more distinguished than when we first met. A quick dinner turned into four and a half hours, and at the time of writing, we have arranged our next dinner date.

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It had never occurred to me to use Instagram as a valuable source of potential suitors – I had created my own account several years ago purely to provide an inspirational place for fashion for the over 50s. But there was a man who had chosen to follow my posts for over a year and, eventually, curiosity led me to follow him back. He was devastatingly handsome, but at the time I thought nothing of it. Now, though, was the moment to be brave. I sent him a direct message, he responded, we swapped mobile numbers and, several days later, we met up at a bar for a quick drink. I was more nervous about this date than any of the others. The enormity of what I had done suddenly hit that night. Where do you start a conversation when you know practically nothing about a person? Luckily, he took the lead and, with the basics covered, it was easier to move onto genuine, flowing conversation. He gave me a huge hug as we parted two hours later, and told me he would love to keep in touch and see me again. I drove home with a huge, soppy grin on my face.

As my second week of dating was drawing to a close (and after being ghosted for at least the 10th time), I gave Bumble one final chance. To my surprise, two men – with sensible jobs, appropriately dressed for my taste – appeared with charming responses. There was such a spark with one of them that after three days of chatting, we arranged to meet at a London hotel for drinks, followed by dinner at a restaurant he had told me a lot about. This was more like it. Then, on the day of the date, I found a message on Bumble. He was cancelling. He had met someone “for a second date that day, and rather than lead anyone on, I would rather see how it goes”. At least he was honest.

So, what have I learnt after my exhausting two weeks of dating like a millennial? It’s true that, from a positive perspective, social media can open the doors to dating much faster than waiting to meet a man while I am walking my dogs. After all, I have been single for two years, and even though I was not actively trying to date, I had wistfully hoped life might have thrown the right man my way. There are plenty of single men out there, but meeting them is difficult if you wait for an introduction.

I am intrigued to discover how Soey will have survived without modern technology to guide her through the dating minefield. I hope she has learnt that there are gentler, kinder and more natural ways of meeting a man, and that her social circle of friends has expanded. Deep in my heart, I would much rather be introduced to a single man through a friend. It seems safer and more sophisticated. But at least I have taken the first steps to join the future. Only time will tell which will proveto be the winner.

Soey’s story

Girl meets boy; girl gives boy her number; boy actually calls girl. It’s the blueprint for every romantic comedy, except that when Gail tells me a similar tale – of how her friend once fell in love with a chef while she was dining in his restaurant, left her number and went on to marry him – it wasn’t fiction. It was real life. This, I thought, was what dating is meant to be like for a young woman in a big city. Fortuitous meetings and love at first sight. Not sitting on the sofa, bag of crisps in hand, mindlessly scrolling through mirror selfies of topless office managers from Surrey.

But I was born in 1996, which means I am of a generation that came of age in an era when courtships are conducted through DMs and love affairs are started with a swipe of a finger. When I moved to London after university, I did what all single 22 year olds are expected to do and downloaded dating apps with a vague notion that I might meet someone “worth it”. All I ended up having was a relationship with my phone – one plagued with notifications, “dick pics” and unsolicited offers of sex. Catcalling and harassment don’t disappear when you’re dating online. If anything, emboldened by the anonymity technology affords, it’s worse. Post #Metoo, I found the concept of strangers being able to access me from behind a screen, having only glanced at six photos and a hastily written bio, fundamentally a bit weird. So I swore off the apps and accepted my single status. Without the internet, it seemed like the only choice. Approaching people IRL isn’t the done thing any more.

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Cue Gail. I found her glamorous dating history completely fascinating – and fantastical. As a recent graduate in one of the most expensive cities on earth, it would be laughable to try and emulate the sparkling social life Gail enjoyed in 1980s London. But she assured me the means by which she met dates cost her nothing but confidence. She set me five tasks to help me date like a baby boomer. 1) Ask friends and colleagues to set me up. 2) Be brave and make the first move on someone I was interested in. 3) Be even braver and let an attractive stranger have my number. 4) Date someone from my existing friend group. And 5) – the most retro of all – try a matchmaking service.

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Task one – easy, I thought, though it turned out to be like pulling teeth. My friends – completely unused to setting each other up – found every excuse to get out of suggesting people. Admittedly, I do have a very specific type (Timothée Chalamet), but was my pickiness really the problem? With their own love lives to prioritise, they had no interest in putting my dating needs before their own. Matchmaking takes time and selfless energy. You can pay people to do it, after all.

And so I did. Gillian, a matchmaker from Drawing Down The Moon, took me on. “People aren’t meeting like they used to,” she told me. “Romance now means window-shopping on a screen. If you want to find love, you need to be ‘domino dating’ – dating as many people as possible, and doing everything possible. It’s tough, and it’s your generation I pity the most.” Ouch.

After an hour long quasi-therapy session, in which I was asked deeply personal questions (“Why do you think you’re single?”), I got a call: I had a blind date. Lawrence* was 6ft 4in, French-English and 12 years my senior. Was he to be the suave, older man I’d dreamt of? When he suggested going for a round of crazy golf, I had my doubts. Lawrence was kind hearted, attentive, fun - but his self-proclamation as the “life of the party” and willingness to date a 22 year old said it all. He was the same age as me at heart, but from a different generation (the same as my sister – a married mother of a six-year-old, whom I consider an entirely different species to me). Like many of my girlfriends, I’ve longed to date someone older (bored by the immaturity of boys our age), but I found our generational differences cringeworthy – and, after three hours, it was time to make my excuses.

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Luckily, my friend Tom, having got wind of my debacle, had lined up a blind date for me. Arthur* wasn’t my type on paper (his unfortunate Peaky Blinders haircut was an immediate turn off – in the virtual world I would not have swiped right), but we couldn’t stop talking and laughed constantly – not politely, properly. I even ate dinner with him – something I’d vowed I’d never do on a first date (far more of a commitment than sex). But his subsequent incessant messaging on every available platform (Facebook, Instagram, Whatsapp, you name it), made me feel as though I had reinstalled the dating apps. The blind date itself was exhilarating; being glued to my phone afterwards was not.

After two more blind dates (nice guys, no spark), I heeded Gail’s advice to make the first move. At a friend’s birthday party in the country one Saturday night, I got chatting to an Alex Turner lookalike who fitted the mysterious pseudo-rockstar type I’m always falling for. We exchanged numbers, agreeing to see each other the following week. In person, at a Marylebone bar of his choosing, Alex* was charming, funny and intelligent, and we shared all of the same interests. We excitedly agreed on date number two, but in the days afterwards: silence. Was he not interested? Did I misinterpret our connection? Did I do something wrong? I was turning into the doubt-riddled, Bridget Jones-esque cliché that I loathe. Gail had assured me there wasn’t a rule about who should message first, so I asked Alex on another date. It never happened. But it’s true what they say: if you don’t ask, you don’t get.

One Sunday afternoon, with this thought going round in my mind, shopping in a vintage store on Portobello Road, I had my first double-take moment. He was exactly my type. We got talking and it turned out he was an actor/model who spoke three languages (swoon), one of them being my mother tongue, Korean. It was too good to be true and I knew I would regret letting it pass me by. I gave my number to the store owner, asking him to give it to Hugh* with a message to call me if he was interested.

He was. We met the following week for drinks in a Notting Hill pub, where he revealed he found my confidence attractive and lamented the fact that people don’t approach each other any more – I was the first woman who’d ever done it with him. The date went as smoothly as my grand gesture. So did dates number two, three, four and five... At the time of writing, we are onto number six. Are we committed? Well, that would mean choosing between him and a friend I have also started seeing (Gail did, after all, insist I look at my existing friendship group for a date).

Whatever happens, I am now fully committed to dating without the internet. My confidence, both in romance and in myself, has soared since I've taken control of my fate. There are endless opportunities to meet people in the real world, we just need to look up from our phones, be present, be bold and seize them. Gail was right – what is there to lose?