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How to date in your late twenties

Well, you wouldn’t want to die alone, would you?

Your late twenties are a funny old time. On the one hand, some of your pals are still living with their parents and attempting, fruitlessly, to launch a sunglasses brand that repurposes wonky veg. On the other hand, a growing number of them are buying up three bedroom maisonettes in Holland Park and calling their firstborns Caspian Boris Starboy. The world of romance is no different. Some people are still deploying their 3rd XV uni rugby tactics of Avicii and Infernos and Australian gap year students, while others are proposing to their girlfriends using livestock on St Barts. But you just want to go on a couple of dates and maybe not die alone. Here’s how.

Think differently for the first date

first date cinema

Has Hollywood got some clandestine deal going on with Big Restaurant? The movies make it seem like a meal out is the perfect recipe for romance, and that love only blossoms in three courses. (I’m sure First Dates has a hand in this, too — why else do you think that Fred chap is so cheerful all the time?) In fact, a restaurant is a catastrophic way to kick things off. What if the conversation is thinner than vichyssoise? What is she swears at a teenage waiter? What if there’s an incident over the cheese course?

Much better to do something ‘outside of the box’ and unconventional. It is also useful if you can place the onus for entertainment on a third party. I have a friend who swears by London Zoo, while another pal is often found at the Battersea Park crazy golf course of a Thursday evening, another Downe House girl wrapped around his putter. (A word of warning: ten pin bowling is actually a nightmare for this sort of thing. The unique dynamic of the sport means that when you’re sitting down, she’s standing up and bowling, and that when you’re standing up and bowling, she’s sitting down. The only time you get to talk or flirt is in the brief crossover moment from the short walk from the seats to the balls, like awkward strangers in a train vestibule.)

Don’t play games

dating twenties games dice

Good games to play in your twenties: backgammon, chess, the hat game, Articulate, Pro Evolution Soccer, Linkee, Spike Ball, ping pong, Twister, Jenga, that one where we all act like we actually like Archie’s girlfriend, that one where we all hide when Archie’s girlfriend comes in to the pub, that one where we all pretend we’re happy when Archie says he’s engaged to his girlfriend, and Sardines. You’ll notice that ‘playing hard to get’ isn’t on that list, because that sort of game is for 12-year-old girls with Nokia 3310s and unhealthy attachments to Enrique Iglesias (these may not be universal references, I know).

Don’t get too heavy too quickly

engagement ring

We’re all terrified of death, of course, and ultimately each of us has to cross that threshold alone. “Death! The undiscovered country, from whose bourn no traveller returns,” or something like that, though I imagine Hamlet would actually be quite hard work on a first date. (Just ask Ophelia! She kills herself, if you didn’t know.) Yes — the relentless ticking of the clock usually leads us to hurry into things and look panickedly about ourselves as our friends get engaged near the pool at Hotel du Cap and start making batches of sourdough together on Sunday afternoons.

As the end of your twenties approaches, the conventional wisdom says that you should have a deposit on a first home, a pasta maker in the cupboard and perhaps a small dog. So we rush into things, and make poor choices, and panic when we’re rejected, and come in too hot, and ruin everything on date three by talking about government help-to-buy schemes and who will look after your mother if she has a stroke. Slow down, take your time, have fun, and go with the flow (like Ophelia — she drowned herself in a river, by the way).

Be yourself

etiquette electric scooters

If I know anything about girls, it’s that they like one type of guy, and one type of guy only. He should have a degree in aromatherapy and a job at Google. He should have family wealth, but not the Succession type of family wealth that makes you very, very sad all the time. He should be able to ride a horse bareback and have done a season, at least, at the Bolshoi. He should be good with an axe but still have soft hands. He should speak fluent Spanish and his friends should own modern art galleries. He should cook eggs every morning and paint when he can’t sleep. He should look good in the rain and cry openly at funerals. He should make his barber laugh and sing into the ocean. He should be spontaneous without being insane, joyful without being unrealistic, funny without being insincere. And you should be him.

This is nonsense, of course. You’re probably absolutely fine as you are. Good luck. I love you. Please invite me to the wedding.

Here’s the essential guide to digital dating…

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