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The Barriers Older Guys Put Up To Stop Themselves Approaching Women

Below is another extract from my forthcoming book on dating for 40+men. This time it concerns the barriers that men are prone to put up in their minds to prevent themselves from having to approach women, particularly younger women.

Of course, these barriers are false, and based on social conditioning. But they are easy enough to dismantle if you think it through logically.



The reticence that you might feel in continuing to game women into your forties is largely societally-created. Or rather, it is societally-created but it is nurtured, fertilised and hatched in your brain. And as with everything in life, the truth of the matter is not to be found in theorising, but rather by approaching the market with your product (yourself) and seeing how it flies.  For it is the market and the market only (in this case the sexual marketplace) that will tell you whether your product is required or not. It’s a bit like selling a house in that it’s all very well saying your place is worth $2m, but before a buyer has actually put that cash in your account it’s all only so much speculation.

Again, my own personal experience has demonstrated to me the degree to which our preconceptions around the way we will be received are largely generated by society and our minds. When I was, up until quite recently, working in my corporate job, I was surrounded by some people who were a similar age to me, and others who were a lot younger (junior staff in their early-to-mid-twenties). Within the work environment there was no segregation between the two groups, as the the industry I was in was pretty social and inclusive, but there was certainly an underlying awareness of the age gap.

‘The young ones just like to go out and get drunk every night’, a colleague of my vintage might say to me. ‘I just can’t do it anymore, what with the kids and the wife. That’s what age does for you.’ And yet personally I felt that I had more in common still with the 25 year olds than I did with this greying man whispering in my ear.

‘Ah, but that is the illusion of every person who gets old—that they are still young ‘really’, like they were in their youth’, you might say. And yes, that is true. And in myself I try to guard against an unrealistic Peter Pan-type attitude. Above all, it is important to look in the mirror and be honest with oneself.

But at the same time, what this greying gent did not know was that in the mornings before work, in the evenings after it and at the weekends I was regularly approaching girls in the streets, in shops and on the underground. Many of these were younger than me—not intentionally, that’s just the way it panned out—and few if any raised my age as an objection. In fact a great many were flattered to be approached and flirted with me normally. In other words there was a disconnect, I realised, between my experience of the realities of the sexual marketplace, and what society and my mind were telling me should be the case.

Remember: evidence procured in the field always, always trumps theory. And the evidence that I was collating by cold-approaching up to ten girls a day was that actually I remained a very viable ‘product’ on the sexual market.

If you don’t believe me then it’s worth trying yourself. Approach one hundred girls. Go out today and approach ten and then do the same thing for the following nine days. You can do it out-and-about in the daytime or in bars and clubs, it doesn’t really matter. For the purpose of this exercise is not so much to make something happen—although of course it will be great if it does—as much as to determine the kind of response you are getting from the market. As always, the market doesn’t lie, but it can be misrepresented if only considered with reference to a small sample size. That’s why you need to approach a minimum of one hundred girls so that you can glean enough data to really know what you’re talking about.

Now, if a very high proportion of the girls you approach say ‘Ewwww, fuck off, you’re old enough to be my dad!’ then you will know that there is a problem that needs addressing. Panic not, though, because even in this circumstance it is more than likely that a simple adjustment in the way you dress, groom or present yourself will make all of the difference.

But what is far more likely to happen is that you will receive much more muted, varied selection of responses than that. And here’s the thing: unless you really look like Larry David after a particularly rough night then you will be surprised how few of them will be related to your age.

‘Yes, but they’re just being polite,’ you’ll say. ‘They’re conscious of my age really, it’s just they haven’t mentioned it to be nice.’

Well, some of them, maybe. But here’s the thing, any player is going to get turned down by some girls. It’s just the way of the world. It sucks, but there it is. No one can achieve a 100% success rate at this: unless maybe you’re Bieber or Clooney, and even then there will still be women out of your reach.

Why? Because everybody has a niche: or rather, everybody has a series of interconnecting niches of which they are a part. If you’re a young surfer guy, then you’re part of the ‘young surfer guy’ niche. If you are a banker working on Wall Street or in the City of London then you are part of the ‘banker guy’ niche. If you have blonde hair and you work as a banker then you get niched down again as part of the ‘blonde banker guy niche’.

Not every girl is going to be into every single niche. It’s just not possible. If a girl is a huge Marilyn Manson fan and dresses like a goth then it is likely that she will be into guys who are similar. It is unlikely—although not impossible—that she will also be into ‘blonde banker guy’.

The point is that not every girl is going to be for you, and not every girl is going to like you. And the job of the player, no matter what age he is, is to go out there and find those girls who are into him, or at least, those who are potentially interested depending on the degree of charm that he can bring to the interaction.

Being an ‘older guy’ is just another niche like any other: some girls will love it, others won’t. And by the way, ‘older guy’ isn’t the only niche you’ll fall into by a long way. Perhaps you are a biker who wears denim and leather and lives to ride across country. Or maybe you’re a poet with long, Byronic hair who lives in a Parisian garret. Or perhaps you are a Silicon Valley whizz who just invented an incredible app. Whatever your personal ‘unique selling point’, it will augment the niche you are in and make you attractive to a wider range of women. Age, in the end, is just one part of the puzzle. Rather than concentrating solely on it, you are better advised to consider it in the context of your other characteristics and to lean into these.

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Jaq - December 7, 2017

Can’t wait for this title to be released! You have just found a niche

    tfadmin - December 8, 2017

    Cheers man! Troy

Ray - December 12, 2017

Hi Troy,

I just read your articles on 40+ men. This is so awesome 🙂

You know, I am at the time of my life, that I have just these very same thought processes like what I read here on your website… And it’s simply awesome to see other men doing so too.

I am dating mostly girls in their twenties. They usually don’t care about my age so much. But one time, I told a girl my (real) age and she got pale white in an instance. We was 21 and we had only kissed once before that discussion. I never heard back from her.

So, should we talk ourselves jokingly around the question or let her guess a younger age? Currently, I say something like “it’s a secret” or “age is only in your mind”.

Looking forward to reading your new book,
Ray from Germany

    tfadmin - December 12, 2017

    Hey man, many thanks! I’m in berlin right now! It’s a tricky issue. I would never recommend lying. However, I think being evasive or ambiguous is fine – in the early stages. If you start to get into a relationship with her then you should come clean. I did this with my ex and she was fine about the 15 year age gap. But by that stage we’d developed a bond. Other girls don’t even bother to ask. So it varies very much from case to case. Cheers, Troy

Tom - December 14, 2017

I am 43 and date mostly girls in their early twenties. I never tell them my real age. It would only make things complicated or even end everything. I always let them guess. Normaly they think I am in between the 25-33 bracket. I’ve noticed young girls are terrible in guessing the age of a guy who is slightly older then them, which is a good thing for me. My advice is to do anything which can make you appear younger. I color my hair to cover up grey hair. I also shave at least every third day also because of grey hair. Do sports to look fit. Dress young but not like a teenager and not to formal. Have a look how stylish men in their late twenties or early thirties dress and copy it. Hell I would even consider some low cosmetic procedures like botox etc.
Be interested in the stuff the young girls like, like the current pop music, books, Tv-series etc. at least to the degree that you know what they are talking about. The good thing is that for the most younger girls it’s not in their reality that a man over fourty approachs them. Don’t crush this illusion!

    tfadmin - December 15, 2017

    Man thanks for the comment and agree with all of this. Sounds like we’re in the same boat. Where are you based?

      Tom - December 17, 2017

      I am german but I am traveling since about two years now. In Germany and I suppose in the most western countries you are put in the “creepy” box when you are over 30/40 and are interested in younger girls. In eastern europe and south east asia it’s not that big deal. Your higher value as a westerner compensates also a lot.

        tfadmin - December 17, 2017

        Hi Tom, true – although I think if you’re 30 and you’re hitting on a 22 year old there should be no problems there. The creepy thing comes in more post-40, depending on how you look, your vibe etc. But you’re right that in EE plus SEA it’s less of a deal. Cheers, Troy.

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