Have you ever slept with or been in a relationship with a cougar?

We were having a couple of beers with a few mates last week and, at a table near enough to us, there was a good-looking woman, in her late forties, who looked like she was pretty well off. Accompanying the middle-aged mommy was a guy who couldn’t have been much older than 27 (so I would say there was about a 20 year age gap between them).

Naturally the banter between my mates dialled up a notch and, while we agreed there wasn’t a guy on earth who wouldn’t want to date an older woman, the question we couldn’t all unanimously answer was  – would each of us be able to handle an older woman?

I’m not specifically talking about the physical aspects here (although you would need to be pretty sure of yourself in bed), I’m talking about things outside of the bedroom you wouldn’t even consider, while staring at her cleavage, for the first time.

Let’s be honest here for a second, there is a better than average chance that a single woman, in her late forties, is a divorcee who has an ex and a couple of kids. Those kids might only be a little younger than you and probably rocking more facial hair. The thought of dating an older chick seems pretty sweet, but consider what your Friday evenings might be like when she has the kids with her and the four of you are sitting around watching TV. You are only a couple of years older than her eldest son, the only difference is that you are sleeping with his mom, and he can read it all over your face.

Older kids and a pissed off ex, aside, are you confident enough to handle a work or family function with your new older lady?

Picture the scene – It’s the year-end work function, and you are surrounded by a bunch of top executives. These guys are in the R3 mil per annum salary bracket and the stuff they are talking about involves skiing holidays in the Alps and R5,000 bottles of whiskey. As a guy in his mid-twenties, still making his way, you are probably nursing a Castle Lite to make sure you don’t get too buzzed before you drive home and occasionally chucking in a story or two about your 2 year stint as a deck-hand in the Med. It’s awkward, and not because money and what you do for a living counts for everything, but unfortunately it does count for something. And the wider the gulf in age, the more apparent experience and money becomes. It’s really pretty evident when you have little of both…

Picture a Christmas lunch, with her family – her old man whispers in your ear, while he pours you a juice and water, “Lighty, I’ve got underwear that is older than you” – again, not something you’d consider on that first date, would you?

Let’s assume you are a ‘Duracell Bunny’ in bed, holding down a pretty good job for a twenty something, and able to hack it, in a crowd filled with guys 20 years older than you. What happens when the hot sex phase fizzles out (and it always does). Do you have what it takes to look after a woman in her late forties, who is looking for something more in her life, than she previously had (yes, I’m talking about being wined and dined and keeping things interesting, well past the initial honeymoon phase)

That’s the kicker…

Want to know why you see so many older guys with younger woman?

The answer is simple – the younger women’s expectations are lower and it’s easier to please them (in every aspect). The reason why the “Ben 10” is as scarce as hen’s teeth, is because, for a young guy to snag at older bird, it takes a lot of balls (excuse the pun), a pretty fat wallet and a lot of energy and commitment.

And for the average bloke out there, it’s far more work than we are actually prepared to do.

“Hey, did you check out that lekker 20 year old at the bar?” That’s more the type of game the average guy likes to play.

Have you ever snagged an older woman? You know you need to share the details with us in the comments section below.


33 replies on “Have you ever slept with or been in a relationship with a cougar?”

The part about having a fat wallet and all the other nuances I disagree ever since I’ve been alive I’ve always found pleasure and sense in older mature women and now I’m engaged to one with three of her own kids and all in all I have seven kids and I’m not even forty but believe me my life makes more sense and I love every minute of it. I can’t handle immature and irresponsible young ones


Yes I had my sugar-mama 30 years older me and what a looker. All I ever wanted sins I left the young and depress girls a long time ago.

So we had a good few months and than she started acting like a teenage girl the, the very thing I wanted to get away, but it was good while it lasted.

I wouldn’t mind getting in a another relationship sins I have learned a lot from dating older woman.

They are very demanding & they know what they want. And I love that.

Dating an older woman is a challenge and if you love challenge it is dating an older woman. I had dated many older woman but they all have one thing in common ” they have tons and tons of love” which sometimes might be boring.

No doubt cougars do look after them selves and that would be the main point of attraction, the fact is women do mature like fine wine, however, a successful older woman would probably be looking for more fun than anything else, you trap yourself by getting used to the life she lives and eventually you start getting clingy and you are shown the exit, like you said, she has kids, no need for more…so the balance in between the sheets and the everyday life challenges should keep you going for a while if you can control yourself, if you can’t, then stay far away, their intuition will immediately pick up what you in for, you’ll be hanging yourself before you start….

Tried it 1nce but the reason was to know why there are many Ben10s, but to my surprise she was great in bed and she never demanded more because she knew I wasn’t making a lot of mulla

Older woman are much more understanding than you think these days.its the younger ones who are aiming for the fat wallets and ski holidays. in all if you do right with either i doubt all the extras will ne important.but i can tell you this you better make dam sure you good in the sack if ur wallets are thin

After reading your blog, I’d say HELL NO!!!! I would definitely do the sex part or do a 2 month fling maybe. THE SEX WOULD BE AMAZING THO HEY!!!!! But to do the lifetime part!!! HELL NO!!! Every guy fantasizes about a older woman and some would follow thru on the whole commitment thing, and kudos to them. What happens when u in your forties and she’s in her 60’s pushing 70??

This is the issue mate, when you’re 40 and she’s 60+ you aren’t going to want her any more for no other reason than she’s just too old!

im 62 now the secret is to date happily marrie women no strings attached just sex then u know what lifes about

These pulchritudinous creatures are very well mannered,when it comes to relationship with younger fellas bcz they’ve got lots of experience when in handle a good guy.Also they know how to take care of home,kids,finances,growth…etc.Most of young fella they enter these relationship in their mind top priority is money and that’s where the problem starts….I prefer older woman rather than these young and depressing chiks..all they consed about is clubing,shopping,nice cars they’ll put u in a competition and then u depressed.

Its gud but it really get annoying when they seek undivided attention. Like u said its extremely embarrassing when seating around her kids knowing her child almost your age. Ijoo! That’s hectic believe me.

the advantage of hooking up with an older woman becomes more evident in your old age. You can both die together !!

Older women have a lot of love and they know what they want from younger guys and most of the time its just great sex, they dont really stress you with expensive gifts and holiday resorts. nowadays its the younger girls who want the fat cats. Hence you see them flaunting material things on social platforms. These young girls arent about loyalty and love, their love is for sale and their loyaly is like a Gucci bag bloddy expensive

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