How to date an older woman

On the hunt for a cougar? Turn your sights on this handy guide

Dating an older woman is a pursuit fraught with difficulty. Colloquially known as ‘cougars’, these rarest of creatures are elegant, elusive, and can often be found in their natural habitats of upscale hotel bars and art galleries.

But, despite the danger, they are beauties worth approaching. Like the big cats from whom they’ve nabbed their nickname, cougars are independent creatures, successful predators and undoubtedly worth waiting for.

So once you’ve squared a Mrs Robinson firmly in your sights and managed to snare yourself an older woman, what do you do next? The goalposts shift when you join the May December club, but make yourself aware of the following unspoken rules and you’ll have your cougar purring in no time.

Dating an older woman 101

This should obviously go without saying, but let’s start with the basics. Unless she’s got some sort of twisted and unhealthy obsession with pursuing much younger men – in which case, run – then it’s likely that your difference in age is simply a by-product of an otherwise standard relationship.

Shape up

She likes you for you, you like her for her, and age – as the old adage goes – is really just a number. Yet although age may not matter, attitude does. If you’re still slouching your way through your twenties, continuing to drink jagerbombs on a regular basis, and leaving the house in threadbare tracksuit pants, she’ll likely tire of you in the blink of an eye.

So, shape up. Dress like a man rather than a boy – you don’t want people playing ‘toyboy or son’ as you stroll by – and start to refine your tastes towards the sophisticated end of the spectrum. This means investing in timeless staples and nailing down a solid grooming routine.

Don't put her on a pedestal

We’re told to respect our elders, to look to them for advice and guidance – but here’s the truth: older doesn’t necessarily mean wiser. She may have several years on you, but she's only human, so will be just as riddled with doubt as everybody else.

So don’t place the burden of the relationship on her. The balance of responsibility and decision making should be split evenly between the two of you, and you shouldn’t ‘follow’. Which leads us to…

Embrace your differences

Being different ages, you’ll likely have different interests, and it’s important not to let them slide. She may not have Tik Tok or Instagram, and will frequently make pop culture references that leave you completely nonplussed, but don’t let that faze you. You’re different people, so celebrate your individuality.

Have confidence in yourself

Be confident about yourself. Don’t squirrel away to hide your app addiction or keep your young music tastes a secret from your significant other. She should like you for who you are, and the right sort of youthful vigour is attractive – as long as you don’t slide back into the dependent and slobby student lifestyle. She’s looking for a man – so be one.

Don't make it all about age

She may be looking for a man, but she’ll never put an age on what a ‘man’ should be. So don’t you try to either. The minute you mention the age difference, or shine too bright a light on it, the whole relationship will descend into the depths of novelty, and you’ll end up reducing each other to nothing more than numbers.

Just be content that you both like each other enough to be together. Don’t worry about the future too much, enjoy the present, and appreciate each other for who you are rather than how many years you’ve been battling it out in the dating arena.

Planning on proposing? These are the cliches to avoid...

Become a Gentleman’s Journal Member?

Like the Gentleman’s Journal? Why not join the Clubhouse, a special kind of private club where members receive offers and experiences from hand-picked, premium brands. You will also receive invites to exclusive events, the quarterly print magazine delivered directly to your door and your own membership card.

Click here to find out more