6 things you discover when you date an older woman

Gareth Rubin on the pros and cons of going out with a cougar

23 June 2017 - 10:52 By Gareth Rubin
Madonna, all-round model for sexually confident women of a certain age, performs in Macau, China.
Madonna, all-round model for sexually confident women of a certain age, performs in Macau, China.

Cougars - what a breed. Sexy older femmes who throw out all the rules of society and grab themselves younger men do us all a favour.

And they have a new leader: head of the pack is now the ever-outrageous Madonna, 58, who is believed to be giving Portuguese model Kevin Sampaio, 31, the time of his life.

It's a ball going out with someone older. When I was 36 I spent a year seeing a 46-year-old. You know those pictures in Hello! of a leggy Nicole Kidman or Rachel Weisz on a beach, captioned 'How STUNNING does Rachel look at 47?' That's what Sally looked like to me - everything lithe and beautiful.

It was exciting and different to the other relationships I had had, all of which had been with girls younger than me.

There's an allure to an older woman that can ensnare a younger man. Ralph Fiennes famously left Alex Kingston for Francesca Annis, 18 years his senior; while Wendi Deng, 48, is in the gossip columns at the moment for knocking off a 22-year-old; and Cheryl Whatever-Her-Surname-Is-This-Week, 33, is showing off her baby daddy, Liam One-Direction, 23, on the red carpets.

Yes, all these guys have seen what's behind the curtain, and found out what you only discover when you date an older woman:

1) Age doesn't make you more serious

You can be approaching 50 and still be quite silly. Many women who have gone through marriage and kids and come out the other side want to rediscover the fun they used to have before it all turned responsible for a while.

So, don't be too surprised if it's 5am and you're in an Uber coming back from an underground drinking club that you had to use a codeword to enter, wondering what the hell happened to that period in between being thrown out of the theatre and flagging down a fire engine. Just accept that it happened and move on.

Portuguese male model Kevin Sampaio, 31, is Madonna's latest hunk.
Portuguese male model Kevin Sampaio, 31, is Madonna's latest hunk.
Image: Kevin Sampaio/Instagram

2) On the other hand, baggage can be a drag

If you wake up one morning and want to jet to St Tropez or take legal highs in Amsterdam, it's trickier if there is a high-powered job or kids waiting somewhere for your girlfriend. Her offspring/ important meeting/patient on the operating theatre table will probably take priority.

Pecking orders become more definite as you get older, so don't be too surprised if you discover you're quite far down the list.

3) Experience counts

Seriously, don't knock it. How do you get better at the violin? You practise. Similarly, no one is a natural when it comes to the boudoir - you get the hang of things, relax into it, learn new techniques, have your eyes opened to exotic ideas. It's not just sexy time either - experience tells you what sort of present might be appreciated on your birthday; or when it's good to take time apart; or where the best place is for a three-day European mini-break.

4) Money = fun

Look, there's no two ways about it: spending the evening on Diet Coke in the pub is all well and good, but it's not quite like a first-class flight to Istanbul to stay in a converted monastery with your own hot tub.

As we get older we usually get richer and can afford more exciting experiences and a more carefree time. Spending the evening obsessing over whose turn it is to pay for the pizza and if your credit card will be cut up by the waiter just puts a dampener on the hours together.

If she wants to treat you, let her.

5) You won't miss the mind games

Insecurity breeds anger. Okay, that sounds a bit Yoda, but the point is that older women tend to be more secure in their lives and are, therefore, more direct about what they want and how. There is much less hinting and mysterious silences when you fail to do/say what is silently expected.

Letting someone else take charge of some of your plans is a weight off your shoulders - there's no need to stress about what restaurant to go to or new experience to try on Friday night because it's her turn to arrange it all. Being in charge can be fun, but taking the back seat can be pretty handy if you've got other stuff on your plate.

6) Your friends will be scandalised

And yet desperate for details. Male buddies will mostly be intrigued, while your gal pals will be over the moon at the thought that in a decade or two they, too, will be able to snag a younger, virile lover. They will consider you a feminist ally and probably hold you up to their current boyfriends as an example of a forward-thinking man unencumbered by millennia of patriarchy.

Secretly you just like the nookie with an older chick. - The Daily Telegraph

This article was originally published in The Times.