A Middle-Aged Woman’s Manual on Dating a Young Man

A Middle-Aged Woman’s Manual on Dating a Young Man

In my upcoming novel, a middle-aged woman dates a thirty-something man.

I say, sometimes it must be hard to be the friend of a novelist. Because all your writer friend ever talks about is that crisis she’s having with the second cousin of her female lead – you know, the one who was supposed to leave her husband, except she can’t find a reason for her to walk out of her marriage, which is why your friend keeps talking about her book all evening long. Or then she’s having a writer’s block, and all she does is stare at her plate bleakly, eating little and saying even less.

I must confess. At times my girlfriends have suffered from the same syndrome with me. (Hi, girls! Promised –  no book talk next time we meet!)

Except that our roles were reversed a year ago, when I was writing my upcoming novel, The Thousand Tiny Miracles of Living Twice. A mixture of chick lit and fantasy – and the first of a feel-good fantasy series – the book narrates the story of a frumpy, middle-aged housewife from Finland who changes bodies with a drop-dead gorgeous Hollywood celebrity.

But that’s not all. Because as soon as she’s inside that perfect supermodel body of 60-90-60, she falls in love with a Justin Timberlake lookalike. He (obviously!) is not a day older than thirty-three.

To cut a long story short, he falls in love with her. Thinking that he’s dating the woman of his dreams. Aged twenty-five.

Of course, the middle-aged woman doesn’t have the courage to tell him the truth.

Now, how’s that for a relationship crisis?

Yet the peculiar thing is that as soon as I told my girlfriends about the plot, they became fiercely passionate about my housewife’s fate. Forget about idle chatter about movies and weekend plans. Oh no. Now we were talking about middle-aged women and their thirty-something lovers, and if such a relationship could really last. Or even happen. It was as if The Thousand Tiny Miracles of Living Twice wasn’t just a chick lit novel. No, this was something personal. This was a fifty-something woman with cellulite and varicose veins. Snatching a thirty-something hunk.

This was… oh my God… political.

Yes, that’s it. Talking with my girlfriends I sometimes felt that I’d got a promotion. I was no longer a mere novelist penning down their next beach read. No, I was nothing more and nothing less than the Instagram age’s Karl Marx and Joseph Engels, breathing life into a new political manifesto. Everywoman’s manifesto.

A manifesto about middle-aged woman and thirty-something men.

And the men look just like Justin Timberlake.

These conversations raged on for months, and the point of them was as follows: if it is possible for middle-aged women to date young men, what are the rules?

Come to think of it, how do middle-aged men do it?

The talks were so rich and passionate that soon I had nothing less than a middle-aged woman’s manual on dating younger men in my head.

Here’s how the manual’s rules went.


‘Honestly, Katarina,’ a mother friend said to me. ‘Listen to me. All you need is a fancy car. Because, let’s face it, it’s a statistical fact that when men have a midlife crisis, they get rid of their first wives and buy a Porsche. That’s how they get that gorgeous twenty-something girlfriend.’

I looked at her. Her husband, a lawyer, drove a shiny Audi SUV so big that whenever she borrowed her husband’s car to do the school run the access road to the school was blocked for a good twenty minutes.

Then I thought about her car. Or mine. They were both old hand-me-downs with license plates dating back to the previous millennium. Not to mention the layer of handkerchiefs, candy wrappers and parking tickets that covered the seats. Or the stains of dog vomit, which simply didn’t go away.

(‘Patience, signora, patience,’ the dog breeder had told me when I called to tell him that the puppy we bought from him regularly emptied his stomach on the back seat of my car. ‘He’ll stop… One day.’)

So, yes, maybe she had a point. Because would Justin Timberlake ever sit in a car covered in parking tickets?

With a whining puppy vomiting on the back seat?


But not all of my girlfriends were satisfied with how my manual had started.

‘Power,’ said another friend. She was a university researcher, so she had to be in the know. ‘It’s a question of power. Study men in politics. Look what happens to them when they gain power. Look at Trump. Or Hollande. Or Bill Clinton. Or even JFK. What unites all these men, if not the fact that they’ve had affairs with young women?’

And then of course, she said, smiling gloomily, there was the Italian bunga-bunga contribution to this rule, with Berlusconi outshining everyone with his wild parties and harem of showgirls.

‘Believe me,’ she insisted. ‘It’s power. That’s all there is to it.’

But others didn’t buy this.

‘Yeah right,’ one of my friends said. ‘And could you imagine women doing anything similar? Like, Angela Merkel boasting in a secret video clip that she regularly grabs the private parts of her male assistants? And later on dismissing the whole thing as aerobics lesson locker-room talk?’


My manual took a quantum leap forward when a fashionista friend of mine heard about the plot of The Thousand Tiny Miracles of Living Twice. An owner of a boutique in the trendy parts of Florence, she’s a woman with a certain kind of presence. Not to mention that she’s dating a man eight years her junior.

‘Oh, honey,’ she sighed. ‘Come on. Don’t be so naïve. You really think a frumpy housewife could date a Justin Timberlake lookalike?’

Yes, but. Don’t men do it?

‘And Madonna did it,’ she replied. ‘And Demi Moore. But you know what Madonna and Demi possess, apart from money and fame?’

I looked elsewhere. I didn’t care to answer.

‘Madonna and Demi both have bodies every twenty-something would die to have,’ she explained to me patiently. ‘And it takes an entire war of attrition to get a body like that. You must suffer. You must sweat. You must starve.’

So, that’s it, then? The third rule of my manual actually works?

Which means that middle-aged women can date young men. But only if they’re willing to torture and starve their bodies like nothing since the Spanish Inquisition.

Ah… It was slowly dawning on me that compiling this manual was not going to be easy.


At some point, things got serious.

‘Don’t you dare let that Justin Timberlake hunk dump the frumpy housewife,’ my mum friend warned me once the first manuscript version was finished.

‘This is a question of rights,’ she added, looking at me almost accusingly. ‘Human rights.’

Ouch. Something told me that if I made the wrong plot move, half of my girlfriends were not going to talk to me any longer.

Thus, I had no other option but to add a new rule into my embryonic manual.


After Madonna and Demi Moore, there was no turning back. The conversation turned pragmatic and even rather cynical.

‘Money talks,’ the boutique owner insisted. ‘If you’ve got money, you can have all the Justin Timberlakes in this world. Even if you look like a walking, Botox-ed zombie. With a serious cellulite problem.’

Someone remembered Leona Helmsley, the New York based hotel billionaire nicknamed the Queen of Mean. Not only had she been notoriously unkind to everyone around her, but what’s more, for sure she hadn’t looked like Madonna or Demi Moore.

No, she had actually looked–

Well, nasty.

Did this mean that the only rule that really mattered in my manual was the last one? Money?

But that question simply led to another one. Namely, did Leona Helmsley date young men?

A friend of mine, an American woman, looked at me. She smiled apologetically.

‘The thing is,’ she said. ‘Leona Helmsley was into… lapdogs.’

‘When she died, her Maltese became the richest dog in the world.’

I didn’t know what to say.

‘And the most hated, too,’ she continued. ‘Trouble was the dog’s name.’


It was the Queen of Mean who opened my eyes.

When I came back home from that girls’ evening at the cinema, I looked at my Bergamasco shepherd dog with new, fresh eyes. Because, let’s face it, that dog has never asked for much. All he wants is a little bit of kibbles and affection.

What’s more, after a handful of dog obedience lessons, he sits down when he must sit down, and he stops barking when he must stop barking.

Plus, maintaining him doesn’t cost much.

And… He is four years old.

Which converted to human years means that he is exactly the same age as my Justin Timberlake lookalike in The Thousand Tiny Miracles of Living Twice.

So, listen to this.

I’m middle-aged. I’m no Demi Moore.

I’m not a New York based hotel billionaire. I drive a car that is a far cry from your average shiny Porsche.

But still, there is a thirty-something male who follows my each and every step.

Who would give his dear life for me.

Now who said that women can’t have it all?




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