Silver Foxes – The Pros and Cons of Dating Older Men

dating a rich old man

I always thought it was the historian in me and a fascination for the past that explained my attraction towards older men (I could listen forever as they tell me about how hard life was during the war 😉 ). However, the fact is I am not alone in my love of the Silver Fox. It seems that many of my peers too are with me on this one. So what is that draws us pretty young things to these grey-haired, wrinkly, antique relics from a bygone era? And more importantly, what are the red flags our innocent minds should look out for when on the hunt for a sugar daddy?

Much of the reason young ladies are attracted to older men boils to down to MONEY and Power. Yes, I’m afraid it is true…there is a little bit of a gold digger in every one of us. Lets face it, a gentleman in his 40s or 50s is more likely to be established in his career (I can totally understand why Monica Lewinsky did Bill Clinton), own property and drive a fancy car while a guy in his late 20s/early 30s probably splashes his cash on craft beers and lap dances at Mavericks. Having money and knowing how to spend it wisely is attractive to a lady.  Lets just say that if Fifty Shades of Grey was set in a township, mummy porn would have really never taken off in such a big way.

I think it’s fair to say that with age comes wisdom. A man who enjoys the finer things in life such as good wine, fancy food, theatre, literature, etc. also has more to talk about than boys our age (yes, it really would be a push to call them men) who can at most discuss the intricacies of computer games, football and the porn industry (topics which will generally fail to hold the attention of any educated person for more than a few minutes).

But now let’s consider the flip-side of all this. Why are these eligible Silver Foxes still single at such a ripe old age? They are:

a) Divorced (and with that comes baggage aka kids – do you really want to play Mummy when you are still a kid yourself?)

b) Not divorced. They just left the wife and kids at home. (Been there, done that and the fool had the audacity to lie about his age, saying he was 39 instead of 49 and I was the even bigger fool for falling for it).

c) A commitment-phobe (they are NEVER going to settle for anyone. Don’t kid yourself. The day you turn 30, your sugar daddy is trading you in for a younger 21 year old model. FACT).

d) Someone who ‘wasted’ their youth being all career focused and now they are married to their job (not always a bad thing but just understand that you will always be second best).

And have you ever considered that it might not be the bloke that is the problem? Might be time for us to be a bit self-reflective ladies. What the hell is wrong with you – dating a man old enough to be your father? Ewww. Daddy issues perhaps? Consider the fact that as attractive as these Daddy-O’s may be, there is going to be a time when the age difference becomes an issue. For instance, how about the day you wake up full of energy and decide to hike up Table Mountain but the relic just had a hip replacement, so it’s not going to happen. What about when his pension money runs out and he can’t take you out dancing in Camps Bay? And then there is the all-important bedroom department, remember you are still a spring chicken, part of the Sex and the City generation, and fully ready for a marathon session of passion but have you considered how you’d feel if the little blue pill doesn’t work on the Old Codger? Just saying.

Now over to you dear readers. We want to know your views on male cougars.  Are you a fan or do you steer clear of Old Timers? Do share your stories – the Good, the Bad and the Wrinkly.


  1. I don’t think that I have ever been considered being interested in ‘silver fox’ or a ‘sugar daddy,’ although I have definitely chatted with them over lots of craft beer, on their tab… I guess it would be fair to say that I am open to a friendly relationship with them. After all, I generally get along with with guys my dad’s age well – watching rugby, enjoying a refined palate when it comes to wine, beer, and food, and love to hangout – it’s pretty easy to get along. There is also no sexual attraction interference, so I feel much more relaxed.

    Last thing, I am a little confused to what age group silver foxes and sugar daddies belong to, and would like some clarification? Who knows, maybe I could fall in this category… I was interested in one guy who was 40 years old last year (10 years older than me), but, oh my, did he have baggage (ex-wives and children issues). Not sure if I will venture down that road, any time soon.


  2. Thanks for checking out the post Patricia

    Its one thing getting on with the Old Timers and another thing to do them ;). There are those that you can hold a civilised conversation with and then there is George Clooney that can get an invite into my bedroom any day 😉

    I guess the appropriate age gap is something that needs to be defined by the individual. When I was in my early 20s I decided 8 years older than me was the max age gap I could go for without being completely eww’d out. But now as I fast approach 30 (please shed a tear for me) I am having reassess… I think I’d consider anyone over 40 or so a Silver Fox. I guess if they were out boozing and shagging (yup they start young in the UK) when I running around in diapers singing nursery rhymes…I think that is a pretty big age gap 😉

    Look forward to hearing more of your views soon 🙂 x


  3. I haven’t dated anyone my own age since high school. No bad experiences so far. No one old enough to need the pill though. I stick to the twenty year gap.

    Liked by 1 person

    • Hi. Lol, so we can establish that as long as they don’t need that little blue friend, then its all good 😉 A lot can happen in 20 years but at least they’ll have some life experience.


  4. Silver foxes don’t appeal to me mostly because I’ve never been into guys who are superior to me in financial terms. I find it intimidating not charming. I much prefer dating guys on a similar level, but as you know I’m easily pleased when I see that a person cares about me. Also, the love for finer things is a personal thing which, I think, is to be attributed to one’s character and not their age.

    Liked by 1 person

  5. Things (another word for men) with age have more character…why are the artifacts in the antique shop so valuable? Because they are OLD. Just like the Silver Foxes.

    Don’t ever be intimidated by money. Embrace it. See it as an opportunity to learn or do something new, that you may not otherwise be able to afford. If a ‘Christian Grey’ type wanted to fly you to Paris in his private jet or take you sailing around the world on a luxury yacht…don’t say you’d would be all like ‘No sorry, there is a broke ass hill billy who I’d rather walk on the beach with’.


    • I can understand zlotybaby’s point of different financial means and it being a concern. If it is seen as a power point in the relationship, then I would prefer to be with someone who is more in my range… haha, or more in the range I want to be, since I am presently a broke student. Someone who can afford themselves financially is totally awesome!


      • I do agree with you to some extent. The minimum is that they should be able to pay their way. But it really sucks when a guy is broke-ass. Its like there is only so much walking on the beach or watching movies at home a person can do. Then say you want to go for a dinner and the only way to afford it is you pay for the both of you. As a once off its fine, but when it gets to the point that its restrictive its no fun. So I’d say he has to be the same or richer.

        There is also a difference about my attitudes towards a guy that I’m just dating and someone I am in a relationship. If we are dating and he is still trying to win me over then money will help but if he has already got me smitten then its fine to go halvies. 🙂


  6. This post is good and made me laugh even. Lots of truth here. I’ve always gone for younger, but tried the most young yet on a recent adventure. The mental capacity connection just wasn’t there, so there are the disadvantages for the older guy too (not that I’m very old.) I guess some guys don’t care about that connection and just want a young body with a pulse.

    Liked by 1 person

    • Hi 🙂 Thanks for checking out the post. Its good to get a male perspective. Sorry if I was a little harsh. Fair dos tho to the old guys tho ,.. if they are still in the game at their age and can cut it with the younger generations, then they must have good game. And some of 20 somethings are cleverer than others…there are some of us that aren’t wasting our youth getting boozed up and are instead locked up in the library studying. 😉

      Liked by 1 person

      • It’s fun being harsh and I loved reading it. I’m kinda surprised by my experience. In my late 20’s a 20 year old would be like “ohhh, you’re too old” hahaha, but now in my mid 30s there are 20 year olds always wanting to hook up. I’ve found that the perfect age (for me) seems to be 25-35 for personality and life-experience reasons (with occasional exceptions.) It’s seriously a great idea to avoid the party life and relationships when young. Plenty of time later for that as it takes a toll too

        Liked by 1 person

  7. […] As part of the smartphone generation, we use Tinder to help us in our quest for love. I’m out and proud about my use of this app, unlike the majority who are embarrassed to admit they are on Tinder (they don’t want their highbrow friends to know that they looking for a hook-up with a HOTTIE half their age). […]

    Liked by 1 person

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