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PEOPLE

It’s a date: there’s a first time for everything

Cosmo and Dolly navigate the emotional minefield of modern dating

Dolly Alderton
The Sunday Times
Cosmo and Dolly
Cosmo and Dolly

Twice divorced, Cosmo Landesman, 61, has proposed and been turned down five times. He recently ended a clandestine relationship, but still dreams of finding true love.

I don’t think it’s fair to dismiss a bloke as bad in bed before you’ve even been to bed with him. But that’s what Justine (not her real name) does. She says: “Sex with you would be so vanilla!” By that she means bland sex. Boring sex.

It’s an odd thing to say to a man you’ve only met 10 minutes ago. But then Justine is only into S&M sex. She is a sub (submissive) looking for a dom (a man to dominate her). And I’m a nice Jewish boy looking for love.

We meet for afternoon tea at a classy hotel. Justine looks like an expensive hooker. Over tea and scones, she shows me various pictures of herself. Justine trussed up like a turkey. Justine on all fours. Justine in chains. So I show her pictures of me. Here’s me as a baby. This is my cat, Marlene. This is my mum. Here’s me making funny faces with my son.

Justine is an educated and intelligent woman with two ex-husbands and no children. She talks about her life as a practising sub all afternoon. S&M is her religion, providing her with the rituals and rules that give meaning to her life.

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“Where,” I ask, “does love come into all of this?”

I can tell she is flummoxed by the question. “Love? It can be very loving, in a subservient sort of way.”

She offers to show me what it’s all about. “Come on, Vanilla Boy, you need to get out of your comfort zone.”

I agree and go back to her place in Mayfair. Her flat looks like something out of the Joan Collins film The Stud: all chrome, mirrors and shaggy carpets.

“I’m just going to slip into something more uncomfortable,” she says. She comes back wearing a black leather bikini with spikes and carrying a saddle, handcuffs, rope and what looked like a thing for cutting pizza.

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She stands there waiting for my masterful demands.

“If you don’t mind terribly, perhaps you could get down on your knees, but only if you want to,” I say.

She shakes her head in despair and gets down on all fours. I get down on all fours by her side. “No!” she says, and nods to the saddle. I get up and place it on her back. “What,” I ask, “do I do now?”

Through gritted teeth, she says: “Get on top!”

Reluctantly I climb aboard. I’ve done doggy but never horsey. I feel more like Lester Piggott than the Marquis de Sade, so I get off and say, “Sorry, this isn’t for me.”

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Justine offers to swap roles. But I don’t take her up on her kind offer to tie me up, put me in a black leather gimp mask and leave me in a cupboard for the rest of the evening.

Instead I head home. I think, in the future, I’ll just stick to vanilla.

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Dolly Alderton, 27, has form: her previous dating adventures include a fling with a Tinder playboy and an on-off relationship with the Comedian. Now she’s not sure what she wants.

It’s 3.15am on a Saturday, and I have broken my three-drink rule and got spectacularly pissed on the first of the summer wine, so I ring for an Uber. I am given the new option of “Pooling”, which means you wait a bit longer and share the car and fare with someone heading in the same direction as you.

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This option hasn’t been around for that long, but I’ve already heard a plethora of urban myths about people meeting their boyfriend/husband/best shag of their life in an UberPool. And when it comes to urban mythology, I try as hard as I can to get in on the anecdotal action. I want to be the Aphrodite of urban mythology, so I give it a go.

Ten minutes later, a Toyota Prius arrives and sitting in the back is a grumpy-looking man and a woman who is a little worse for wear. “Hello!” I say, like we’ve been seated next to each other at a wedding. “I’m Dolly. This is my first time doing UberPool. Do you know each other?”

“We are couple,” he says blankly. “We go to Wood Green.”

“Is she OK?” I ask, gesturing at his girlfriend, who is limply hanging her head out of the window.

“No, she is not OK, because she drink too much, even though I tell her not to, and now she feel sick.”

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“Oh dear. Shall we get you some water?”

“No, I am fine soon,” she croaks.

I learn a bit about the pair of them from the grumpy boyfriend. They’re both Czech PhD students, have been living in London for five years and are about to move to Florida.

“How long have you been together?” I ask.

“Eight years,” he replies.

“But he will not marry me,” the girlfriend slurs.

“Why won’t you marry her?” I ask.

“I don’t want to get into this,” he mutters. “It’s just a bit of paper.”

“Well, if it’s just a bit of paper to you, but it means so much to her, why don’t you do it for her?”

“Eezakltly!” she shouts at him.

“Look at her,” I say. “She’s beautiful. And she’s really clever, she’s doing a PhD. And you’re in the same line of work. She’s your dream come true.”

“I know this,” he barks.

“Well then, why won’t you marry me?” she asks.

“I think you should just do it,” I say.

“Weddings are too expensive,” he replies.

“Not necessarily,” I reply. “I’ll give you a number for a pub that does a very reasonable reception.” He rolls his eyes.

The cab pulls up outside my flat and I say goodbye to my new friends, knowing their drunken argument has only just begun and will probably rumble on all weekend.

And as I get into my big, empty bed, I feel so lucky not to have to argue with anyone.

@dollyalderton