How has Dating Changed as I’ve Gotten Older?

Listen to the audio version of this article:

“Hey Andy, how has dating changed as you’ve gotten older?”

One of my coaching clients asked me this question recently, and there’s a ton I want to say on this. Dating, for me, has gotten easier as I’ve gotten older. Now, let’s add in the caveat that I have obviously been improving myself the entire time.

I have been working really hard on myself. I’ve worked on my confidence, my body, my looks, my sense of self, my honesty, my openness, my vulnerability, my ability to talk to women, my sex skills, my sexual repertoire, and much more. I’ve been working on all of this over the last probably eight years at this point.

My coaching client, on the other hand, hasn’t been working on his sex/dating life for all that long. But he feels like he’s running out of time – like one day it’ll be too late for him. He worries, “Is time running out when it comes to dating and meeting women? When I’m 35, when I’m 40, when I’m 50, will I be too old for this stuff?”

Let’s be honest, a lot of you have this fear. I certainly did. A lot of women have the same fear too; a fear of getting old. The fear that nobody will love you, nobody will want you, nobody will think you’re attractive anymore. The solution I’ve found in my own life – and the lives of all my coaching clients – is to spend every day/week/month improving yourself in just a tiny little way.

It can be your appearance, it can be your mental headspace, it can be working towards enlightenment and being a more peaceful, happy, loving, giving, joyful person. It could be getting more interesting hobbies., or learning, or growing, or chasing your pursuits, or making more money. Whatever it is, as long as you’re moving forward every day in some of those metrics, that’s what really matters.

And you’ll find if you just improve yourself over time, you will be a better prospect the older you get (especially if we’re talking about men). You will be improving yourself every single week, every single month, every single year, s that when you’re older, you will be a better product.

When you’re 35, or 45, or 55, or whatever age it is that you’re worried about being too old when you’re that age, if you have spent every day between now and then improving yourself, you will literally be a more appealing man.

And this applies to women as well – always be improving yourself, and you can make yourself a better product. Now, there’s the caveat with women that, generally speaking, most guys like younger women. Sure. But you can still be improving yourself as a woman, rather than completely giving up. You don’t have to just resign to Father Time and say, “I’m going to get less attractive over time, so what’s the point in fighting it?” No. Spend every single day of that working on yourself, making yourself a better human being.

As for the original question of how dating has changed for me, personally? It’s gotten easier because I’ve worked on myself. It’s gotten soooo much easier.

It is so much easier now for me to meet new women, for me to have an awesome time, for me to be completely honest with them about all of the kinky stuff I want to do with them, and all of the kinky stuff I want them to do with my lovely girlfriend Imogen.

All of this stuff is so much easier than it was when I was in my twenties and thirties. And it only keeps getting easier. I give less of a fuck than I did when I was younger (“abundance mentality”). I’m a much more confident, calm, rational human being at 35 than I ever was when I was in my 20’s. There are so many parts of yourself you can work on and improve so that by the time you hit my age, you’ll be an absolute beast.

But as well as being easier, I’ve noticed I’m much more polarising the older I’ve gotten.

When you’re in your early 20’s, most of the people you hook up with will be around your age – it’s considered pretty normal by most mainstream accounts. But when you’re 35 and hitting on 20 year old women, that can be more polarising. There are some women who just won’t date an older guy. Especially at this point where I’m 15 years older than a 20 year old woman. Some of those women just won’t be into me, which is totally cool.

However, some of the younger women won’t really care about my age – they’re ambivalent about it. For them, me being older is neither a good thing, nor a bad thing. So with these women, as long as I’m still full of energy, ambitious, dress well, mentor them, help them explore their sexuality, am an interesting person, treat them well – quite a few of these “age-ambivalent” women will sleep with me/date me.

And then there’s a third category of younger women: the younger women who want older guys. They sit around fantasising about it. They sit around daydreaming about an older man to save them from all these retards who are their own age. These women want to date older men and will actively seek them out – see what I mean about the older you get, the more polarising you are with younger women?

I find this absolutely awesome – it means the girls who don’t like me because I’m older, will absolutely make that clear – and nobody’s time gets wasted. Awesome. And the girls who love older guys will absolutely make that clear – saving us both time and leading to much more passionate and fun sex. Awesome. All of this means I find it much easier to have sex as an older guy.

Another point to be made is: my potential dating pool has opened up the older I’ve gotten. Speaking very generally here, most women prefer guys who are their age or older. Most women – generally speaking – don’t date younger guys. So if you think about it, the older I get, the wider age range of women I have access to. When I was in my early 20’s, not as many 30 year old women were into me (not to mention, I felt too “young” to be hitting on them). Now that I’m 35, 30 year old women will happily sleep with me (and I feel more comfortable hitting on them).

I know a lot of you have fears of, “What if time runs out for me, what if I don’t hurry up and handle my sex life before it’s too late?”. You worry that when you’re above a certain age, it’ll be “weird” or “creepy” to hit on women and care about your sex life. But fuck that; weird is just a story. If you’re a 50 year old guy and you want to hit on younger women, as long as they’re legal ae, as long as you’re polite, and as long as you accept the word “No” – then go hit on them. If this is something that’s important to you, go chase your dreams. Don’t concern yourself with what anybody else might say about it.

Hell, I coached a guy last year who was 59, and wanted “permission” (encouragement) to go out and talk to younger women. I told him to get his ass out the door and go make some women’s days by hitting on them. And he did. He threw himself in there even though he had a massive fear of “But what if I’m too old?” He had the basics handled: good grooming, wasn’t fat, dressed well, had his shit together, good sense of humour, gently good guy. And when he went up to women, they loved it – even the younger ones. Especially the younger ones.

And the ones who didn’t like him? The ones who thought he was too old? He’d just say, “No hard feelings, that’s cool. I hope you have a lovely day.” Remember guys, with all of this stuff – it’s not about getting every single girl to like you. That’s impossible. Your only mission is to talk to a lot of women, and see which ones like you. That’s it. This is a number’s game.

Some of you also worry that girls might be creeped out by you. I’ll tell you right now: yes, some of them will be. You cannot stop that. Some women will hate that you’re older and you’re trying to have sex. Awesome – it’s great they know what they want and don’t want. Wish them a great day and off they’ll go. Your mission isn’t to convince anyone that what you’re doing is “ok” or “acceptable”; no. YOU are the only one you need to convince. So go look in the mirror, stare deep into your own eyes, and say out loud:

“What I’m doing is ok. What I’m doing is good. In fact, my mission is to make girl’s lives better for having met me. I give myself permission to be an older guy, working on his sex life.”

One fallacy we often make is to look around us and see what other people our age are doing. If we find that they’re not currently doing the thing we want to do, we often tell ourselves, “That must mean it’s impossible. After all, nobody else my age is doing this, so it can’t be done.”

And yes, most older guys are not going outside and hitting on women, or trying to have sex. But that doesn’t mean you can’t do those things. If having a lot of sex or having an elite dating life is something that’s important to you, don’t look around at everybody else your age and say, “They’re not doing it, so I shouldn’t do it.” As I said, if this is important to you, go out there and make it happen. We’re here to win, so go play to win.

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And while I’m all fired up about playing to win – some of you motherlovers are sitting there wanting to sign up for my coaching, but your head is full of all sorts of limiting beliefs. “I don’t have the money right now”, or “Now isn’t the right time“, “I don’t know if I’m ready to go all-in yet”, or “I should wait til I move and I’m in a better location for talking to women”, etc.

Fuck that.

Do you know how many of my coaching clients who’ve gone on to do amazing things have had those exact same limiting beliefs in their head… only they didn’t let the bullshit excuses hold them back?

They took a deep breath, grabbed their nuts, took a leap of faith and contacted me.

“Now isn’t the right time, but fuck it. I’ll sign up.”
“I don’t know if I have enough money right now, but I’ll take out a damn bank loan and use your payment plans, Andy. Fuck it.”
“I’m worried I’m not going to be the ass-kicker that the rest of the coaching clients are. Fuck it, I will take a chance and do this anyway.”

Be like them. Don’t be like the fucking person that sits there and goes, “I will let my fears and worries hold me back from taking action.” Fuck that. This is your life we’re talking about. This is it – you only get one. Use this chance for greatness and let’s give you the life you deserve.

Sign up now – don’t dick around. I’ll be putting the price up again soon. More importantly, in the not-so-distant future, I’ll eventually be moving away from coaching (Cam will run my coaching program). So you aren’t going to have much more of an opportunity to have me mentor you – don’t waste your chance.

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