Cougar town: Dating an older woman

Demi Moore’s 6-year marriage to Ashton Kutcher was constantly in the public eye, and the talk was mostly about their 16-year age difference. Net photos

I saw this couple in a bar. It was late in the night, and the clock was slowly ticking towards sunrise. The man was young, you could tell from his sagging pants. He didn’t look a day over 24. The woman on the other hand was a cougar. An older woman. Her face lined with wisdom and old age. It seemed to be past her bedtime. At 1am, at the age of what looked like 100, she must be on dream number four. But here she was, at this satanic hour, seated with a man fit to be her grandson.

I sat in the corner, a drink in my hand, and I stared at them. They sipped slowly on expensive drinks, staring at each other, smiling flirtatiously and tossing to the gods of affection. Love, like a plume of smoke, hanged heavy in the air. The music wasn’t too loud. It was just perfect. Slow. Good music.

It dawned on me that, obviously, she wasn’t trying to help him with course work, no. Neither was she his mother. She was his girlfriend (gasp!) or he was her boyfriend. After, they stepped off their stools; arms wrapped around their waists, and bundled out of the bar. They drove off and got swallowed by the still night.

This spectacle left a storm of questions in my head. Why do young men prefer older women? Maybe, to your end, you might argue that it was a one-off, that I shouldn’t generalise. Fair enough. But still, we can’t completely forget that the dating scene has changed. I’ve met younger folks who would prefer to date significantly older women as opposed to their age mates. Let’s dissect the reasons why.


Most cases, these older women have more money. They bankroll their lifestyles and that’s what a millennial craves for now. If he wants an iPhone X, she can provide. Robert Kelly once said, “When a woman loves, she loves for real.” For purposes of this article, when an older woman loves a younger lad, she loves for real. She goes out of her way. She does the ridiculous and the maximum. Yes, they have baggage, but who doesn’t? She comes as she is, fully equipped; with love and wisdom, with a bagful of experience and thirst, with lots of money and less drama. No Instagram account, no Snapchat filters. She’s not interested in the hoopla online, she’s here for you. Like Richard Quest, she means business. And younger folks love that, who wouldn’t? 

They have seen it all

At her age, her life has hit a plateau. She’s made it in life. Her dreams, most of them, have been achieved. She’s been with Tom, Harry, Ivan, Simon, Moses, and John. She’s seen tall, short, big and really tiny. She’s been here, there, everywhere. She’s seen them. All of them. All shapes and sizes. So, she’s not here to be impressed, because, clearly, you can’t press her. Few things impress her in life. She’s been in love and out of it, broken hearts and had hers broken countless times. And right now, she wants you, she wants fun, she wants pleasure with no pressure.

She has seen the glum and ugly side of life. She has swum the turbulent currents of life, the deeper and shallow waters. Handful of things make her move a muscle, unlike the younger woman whose life is like a blank page, and still has a lot of things to fill it. So, no doubt, young men fancy older women because of their real-life experiences, unlike the young girls who are still embraced with naivety., a social website, breaks it down more clearly that more often than not, an older woman has faced her insecurities and fears head on, and has dealt with them to the best of her abilities.

She won’t try hard to impress

An older woman is like a sleek Mercedes Benz. Have you seen a grand Merc? Mostly a black Mercedes Benz: black as sin, and sleek like mercury. A car that costs a body part. A car that looks like it is constantly disgusted. A Mercedes Benz doesn’t try hard to turn heads around. It doesn’t. It doesn’t try hard to evoke your feelings, or your admiration. And so is an older woman. She won’t try hard to impress. She won’t dress in those little clothes short of fabric, paint her lips and tweeze her eyebrows. She will step out of her house in a dress she deems comfortable. Unlike these young girls who try too hard to impress fellow young boys and older lads, and still fail.


If an older woman decides to love, she will love. Wholly. Deliberately. At this point, I want to think, she’s desperately looking for love. She’s looking for affection, fiercely craving for it. Remember, she’s been rolled in the mud by very many trash men. Here, she wants to be appreciated and respected and loved for who she is. If a young lad loves her right and brings sunshine to her life, she will stick around with him.

Living in denial

In an article published on, common sense dictates that you cannot be 40 years old and single, and not have a significant amount of baggage: ex-boyfriends, husbands, children, business pressures, debts et al. The article, furthermore, states that, like it or not, by getting involved with an older woman, you are putting yourself in a situation where the moral majority, people like your parents and boss, will frown upon you.

Dating an older woman is like riding a bicycle with one wheel. It won’t take you anywhere. Even though you carry it on your back, you won’t go far. At the end of the day, when the dust settles, it is up to you to weigh the pros and cons of such a relationship and decide whether it is right for you, or it will break your neck or your heart. Or both!