As Valentine’s Day heads our way with the express wish of making singletons feel like second-class citizens, single Chelsea socialite Henry Conway tells it like it is in the 21st century world of digital dating  

Single life in London can be quite frustrating. As a singleton in his mid 30s, I am asked on a near daily basis who I’m dating and why a nice boy like me has not settled down yet.

Am I eligible? Well I have my own teeth, and despite my best efforts in the cake department, I’m relatively trim, so why still single? Like many of my generation who didn’t settle in our 20s, I date a bit, but perhaps I am a victim of too much choice.

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I can claim, not unreasonably, that I am one of the most social people in London – be it a launch party, a fashion show, a bar or club, it’s in my DNA to be out seven nights a week. Despite encountering new people every day, I still rarely find someone I click with.

Once, while talking to two of my sister’s twentysomething friends, the chat turned to one of the girl’s newish boyfriends: ‘OMG, I can’t believe you met him IRL’.

IRL? Yes, they were astonished to hear that people got together ‘In Real Life’. The old stigma of meeting a potential partner online is well and truly evaporated to the point of online being the norm. Thus, I too have put myself on every app I can download in my quest for love.

Passing on advice based on my experiences of meeting digitally is something I am only too happy to do. Don’t fear it – be it the girl fed up of being the odd number at a dinner party entirely made up of couples, or the chap who has exhausted his network of singletons, there should be no shame in putting yourself into situations to meet others who are looking for the same thing as you.

I don’t like endless online chats – thankless rounds of unending banter never seem to go anywhere. I recommend taking it IRL as soon as you’re ready

With most apps pooling information from social media to show shared friends and interests, pick up on that common ground when initiating conversation, and never be shy in your due diligence. Message that mutual friend and get the warts-and-all lowdown – highly useful in weeding out the odd charlatan who is playing away from home, before you take it too far.

Personally, I don’t like endless online chats – thankless rounds of unending banter never seem to go anywhere. I recommend taking it IRL as soon as you’re ready. Always try to have something to go on to after that first drink, in case you’ve accidentally met a bunny boiler – though leave it flexible enough to extend to dinner if the chemistry is sizzling. A martini at the Botanist or a margarita at Mr Foggs should set you up nicely.

Make sure you have a fully charged phone so you can look busy if your suitor is late, or should you need to search for a last-minute reservation. Ready for that second date? Don’t bring flowers – everyone will notice, and judge you. A nice rose lapel pin from Tateossian, which you can accidentally leave on a bedside table to ensure a later retrieval, is far more chic.

Overthought this perhaps? Well, no matter how rational a person you are, it all goes out the window when the butterflies start. Look sharp, try and keep your cool, and don’t pressure yourself. In swiping left or right, it’s evident there are plenty of fish out there.

Cast those trawler nets, and with a little luck one day you’ll get the one you don’t want to throw back in.


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